CA2733235A1 - Crystalline forms of a pyridine derivative - Google Patents
Crystalline forms of a pyridine derivative Download PDFInfo
- Publication number
- CA2733235A1 CA2733235A1 CA2733235A CA2733235A CA2733235A1 CA 2733235 A1 CA2733235 A1 CA 2733235A1 CA 2733235 A CA2733235 A CA 2733235A CA 2733235 A CA2733235 A CA 2733235A CA 2733235 A1 CA2733235 A1 CA 2733235A1
- Authority
- CA
- Canada
- Prior art keywords
- compound
- crystalline form
- formula
- disorder
- methylbenzenesulfonate salt
- 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.)
- Abandoned
Links
- 150000003222 pyridines Chemical class 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 110
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- 239000003054 catalyst Substances 0.000 description 1
- 206010007776 catatonia Diseases 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229960003920 cocaine Drugs 0.000 description 1
- 201000001272 cocaine abuse Diseases 0.000 description 1
- 201000006145 cocaine dependence Diseases 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 235000019788 craving Nutrition 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 238000002425 crystallisation Methods 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
- 230000001351 cycling effect Effects 0.000 description 1
- 208000026725 cyclothymic disease Diseases 0.000 description 1
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 1
- 235000018417 cysteine Nutrition 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 208000024732 dysthymic disease Diseases 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000003517 fume Substances 0.000 description 1
- 208000029364 generalized anxiety disease Diseases 0.000 description 1
- 201000002270 hallucinogen abuse Diseases 0.000 description 1
- 201000006138 hallucinogen dependence Diseases 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 230000035876 healing Effects 0.000 description 1
- 208000019622 heart disease Diseases 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- GMZGWPPEZCREPP-SNVBAGLBSA-N methyl (2r)-2-(benzylamino)-3-hydroxypropanoate Chemical compound COC(=O)[C@@H](CO)NCC1=CC=CC=C1 GMZGWPPEZCREPP-SNVBAGLBSA-N 0.000 description 1
- ANSUDRATXSJBLY-GSVOUGTGSA-N methyl (2r)-2-amino-3-hydroxypropanoate Chemical compound COC(=O)[C@H](N)CO ANSUDRATXSJBLY-GSVOUGTGSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 201000003631 narcolepsy Diseases 0.000 description 1
- 208000004296 neuralgia Diseases 0.000 description 1
- 208000021722 neuropathic pain Diseases 0.000 description 1
- 229960002715 nicotine Drugs 0.000 description 1
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000001272 nitrous oxide Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 201000005040 opiate dependence Diseases 0.000 description 1
- 201000000988 opioid abuse Diseases 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 208000002851 paranoid schizophrenia Diseases 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000008177 pharmaceutical agent Substances 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 230000035790 physiological processes and functions Effects 0.000 description 1
- 208000028173 post-traumatic stress disease Diseases 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000000306 recurrent effect Effects 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 208000022610 schizoaffective disease Diseases 0.000 description 1
- 208000025874 separation anxiety disease Diseases 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 201000002859 sleep apnea Diseases 0.000 description 1
- 208000022925 sleep disturbance Diseases 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L sodium sulphate Substances [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 230000000392 somatic effect Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 231100000736 substance abuse Toxicity 0.000 description 1
- 201000006152 substance dependence Diseases 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical class S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000007916 tablet composition Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
-
- 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
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5375—1,4-Oxazines, e.g. morpholine
- A61K31/5383—1,4-Oxazines, e.g. morpholine ortho- or peri-condensed with heterocyclic ring 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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- 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
- A61P25/20—Hypnotics; Sedatives
-
- 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
- A61P25/22—Anxiolytics
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Anesthesiology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0814340.6A GB0814340D0 (en) | 2008-08-05 | 2008-08-05 | Anhydrous crystol form fo a pyridine derivative |
| GB0814340.6 | 2008-08-05 | ||
| PCT/EP2009/060089 WO2010015626A1 (en) | 2008-08-05 | 2009-08-04 | Crystalline forms of a pyridine derivative |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2733235A1 true CA2733235A1 (en) | 2010-02-11 |
Family
ID=39767571
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2733235A Abandoned CA2733235A1 (en) | 2008-08-05 | 2009-08-04 | Crystalline forms of a pyridine derivative |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US8093242B2 (https=) |
| EP (1) | EP2321324A1 (https=) |
| JP (1) | JP2011529942A (https=) |
| KR (1) | KR20110052686A (https=) |
| CN (1) | CN102171219A (https=) |
| AU (1) | AU2009279135B2 (https=) |
| BR (1) | BRPI0917224A2 (https=) |
| CA (1) | CA2733235A1 (https=) |
| EA (1) | EA201170300A1 (https=) |
| GB (1) | GB0814340D0 (https=) |
| IL (1) | IL210777A0 (https=) |
| MX (1) | MX2011001414A (https=) |
| WO (1) | WO2010015626A1 (https=) |
| ZA (1) | ZA201100426B (https=) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102639536B (zh) * | 2009-08-27 | 2015-03-18 | 尼尔医疗有限公司 | 吡啶衍生物的无水晶型 |
| EP3574907B1 (en) * | 2015-05-18 | 2023-08-23 | KaNDy Therapeutics Limited | A dual nk-1/nk-3 receptor antagonist for the treatment of sex-hormone-dependent diseases |
| JP7433252B2 (ja) | 2018-03-14 | 2024-02-19 | キャンディ・セラピューティクス・リミテッド | Ｎｋ－１／ｎｋ－３受容体二重アンタゴニストを含む新規な医薬製剤 |
| KR102950227B1 (ko) | 2019-11-15 | 2026-04-08 | 칸디 테라퓨틱스 리미티드 | Nt-814의 핵심 중간체인 6-클로로-4-(4-플루오로-2-메틸페닐)피리딘-3-아민의 새로운 화학적 제조 방법 |
| WO2025242583A1 (en) | 2024-05-24 | 2025-11-27 | Bayer Consumer Care Ag | Novel formulation comprising elinzanetant in a solid dispersion |
| WO2025242585A1 (en) | 2024-05-24 | 2025-11-27 | Bayer Consumer Care Ag | Crystalline forms of salts of elinzanetant and compositions containing salts of elinzanetant |
| US12533358B1 (en) | 2025-05-14 | 2026-01-27 | Bayer Consumer Care Ag | Methods of treatment with elinzanetant |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE265209T1 (de) | 1996-07-17 | 2004-05-15 | Merck & Co Inc | Änderung des zirkadischen rhythmus mit nicht- peptidischen neurokinin-1 rezeptor antagonisten |
| EP1394150B1 (en) * | 1999-02-24 | 2011-01-19 | F. Hoffmann-La Roche AG | 4-Phenylpyridine derivatives and their use as NK-1 receptor antagonists |
| WO2001030348A1 (en) | 1999-10-25 | 2001-05-03 | Janssen Pharmaceutica N.V. | Use of substance p antagonists for influencing the circadian timing system |
| GB0203022D0 (en) | 2002-02-08 | 2002-03-27 | Glaxo Group Ltd | Chemical compounds |
| GB0203020D0 (en) | 2002-02-08 | 2002-03-27 | Glaxo Group Ltd | Chemical compounds |
| TW200403058A (en) * | 2002-04-19 | 2004-03-01 | Bristol Myers Squibb Co | Heterocyclo inhibitors of potassium channel function |
| SI1643998T1 (sl) * | 2003-07-03 | 2007-12-31 | Hoffmann La Roche | Dvojni nk1/nk3 antagonisti za zdravljenje shizofrenije |
| EP1928886B1 (en) * | 2005-09-09 | 2011-04-13 | GlaxoSmithKline LLC | Pyridine derivatives and their use in the treatment of psychotic disorders |
-
2008
- 2008-08-05 GB GBGB0814340.6A patent/GB0814340D0/en not_active Ceased
-
2009
- 2009-08-04 MX MX2011001414A patent/MX2011001414A/es unknown
- 2009-08-04 WO PCT/EP2009/060089 patent/WO2010015626A1/en not_active Ceased
- 2009-08-04 JP JP2011521561A patent/JP2011529942A/ja not_active Withdrawn
- 2009-08-04 EA EA201170300A patent/EA201170300A1/ru unknown
- 2009-08-04 CN CN2009801393221A patent/CN102171219A/zh active Pending
- 2009-08-04 AU AU2009279135A patent/AU2009279135B2/en not_active Ceased
- 2009-08-04 US US13/056,775 patent/US8093242B2/en active Active
- 2009-08-04 EP EP09781468A patent/EP2321324A1/en not_active Withdrawn
- 2009-08-04 BR BRPI0917224A patent/BRPI0917224A2/pt not_active IP Right Cessation
- 2009-08-04 KR KR1020117005159A patent/KR20110052686A/ko not_active Withdrawn
- 2009-08-04 CA CA2733235A patent/CA2733235A1/en not_active Abandoned
-
2011
- 2011-01-17 ZA ZA2011/00426A patent/ZA201100426B/en unknown
- 2011-01-20 IL IL210777A patent/IL210777A0/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US20110136798A1 (en) | 2011-06-09 |
| BRPI0917224A2 (pt) | 2015-11-24 |
| EP2321324A1 (en) | 2011-05-18 |
| MX2011001414A (es) | 2011-04-04 |
| ZA201100426B (en) | 2012-03-28 |
| US8093242B2 (en) | 2012-01-10 |
| JP2011529942A (ja) | 2011-12-15 |
| GB0814340D0 (en) | 2008-09-10 |
| IL210777A0 (en) | 2011-03-31 |
| WO2010015626A1 (en) | 2010-02-11 |
| CN102171219A (zh) | 2011-08-31 |
| AU2009279135A1 (en) | 2010-02-11 |
| EA201170300A1 (ru) | 2011-08-30 |
| AU2009279135B2 (en) | 2012-09-13 |
| KR20110052686A (ko) | 2011-05-18 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |
Effective date: 20140805 |