OA11955A - Polymorphs of crystalline (2-benzhydryl-1-azabicycloÄ2-2-2-Üoct-3-yl)-(5-isopropyl-2-methoxybenzyl)-amine citrate as NK-1 receptor antagonists. - Google Patents
Polymorphs of crystalline (2-benzhydryl-1-azabicycloÄ2-2-2-Üoct-3-yl)-(5-isopropyl-2-methoxybenzyl)-amine citrate as NK-1 receptor antagonists. Download PDFInfo
- Publication number
- OA11955A OA11955A OA1200100317A OA1200100317A OA11955A OA 11955 A OA11955 A OA 11955A OA 1200100317 A OA1200100317 A OA 1200100317A OA 1200100317 A OA1200100317 A OA 1200100317A OA 11955 A OA11955 A OA 11955A
- Authority
- OA
- OAPI
- Prior art keywords
- citrate
- monohydrate
- crystalline
- anhydrous
- methoxybenzyl
- Prior art date
Links
- 102000002002 Neurokinin-1 Receptors Human genes 0.000 title description 4
- 108010040718 Neurokinin-1 Receptors Proteins 0.000 title description 4
- 239000002464 receptor antagonist Substances 0.000 title description 4
- 229940044551 receptor antagonist Drugs 0.000 title description 4
- 150000004682 monohydrates Chemical class 0.000 claims abstract description 12
- 206010047700 Vomiting Diseases 0.000 claims abstract description 9
- 238000004519 manufacturing process Methods 0.000 claims abstract description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 8
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 29
- YASYEJJMZJALEJ-UHFFFAOYSA-N Citric acid monohydrate Chemical compound O.OC(=O)CC(O)(C(O)=O)CC(O)=O YASYEJJMZJALEJ-UHFFFAOYSA-N 0.000 claims description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 12
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims description 8
- 239000013078 crystal Substances 0.000 claims description 7
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 6
- 239000000155 melt Substances 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 238000001914 filtration Methods 0.000 claims description 5
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- 238000001035 drying Methods 0.000 claims description 3
- 238000003756 stirring Methods 0.000 claims description 3
- 239000003890 substance P antagonist Substances 0.000 claims description 3
- 238000003786 synthesis reaction Methods 0.000 claims description 3
- 230000000694 effects Effects 0.000 claims description 2
- 230000001747 exhibiting effect Effects 0.000 claims 3
- 239000003937 drug carrier Substances 0.000 claims 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 6
- 230000001154 acute effect Effects 0.000 abstract description 2
- 238000002512 chemotherapy Methods 0.000 abstract description 2
- 239000002775 capsule Substances 0.000 abstract 1
- 238000009472 formulation Methods 0.000 abstract 1
- 238000001990 intravenous administration Methods 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 229940093499 ethyl acetate Drugs 0.000 description 4
- 235000019439 ethyl acetate Nutrition 0.000 description 4
- 239000012458 free base Substances 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000002441 X-ray diffraction Methods 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 238000000113 differential scanning calorimetry Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- QDZOEBFLNHCSSF-PFFBOGFISA-N (2S)-2-[[(2R)-2-[[(2S)-1-[(2S)-6-amino-2-[[(2S)-1-[(2R)-2-amino-5-carbamimidamidopentanoyl]pyrrolidine-2-carbonyl]amino]hexanoyl]pyrrolidine-2-carbonyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-N-[(2R)-1-[[(2S)-1-[[(2R)-1-[[(2S)-1-[[(2S)-1-amino-4-methyl-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]pentanediamide Chemical compound C([C@@H](C(=O)N[C@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(N)=O)NC(=O)[C@@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CCCCN)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](N)CCCNC(N)=N)C1=CC=CC=C1 QDZOEBFLNHCSSF-PFFBOGFISA-N 0.000 description 1
- BIUZWZLMPAUPFK-UHFFFAOYSA-N 2-benzhydryl-n-[(2-methoxy-5-propan-2-ylphenyl)methyl]-1-azabicyclo[2.2.2]octan-3-amine;2-hydroxypropane-1,2,3-tricarboxylic acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O.COC1=CC=C(C(C)C)C=C1CNC1C(C(C=2C=CC=CC=2)C=2C=CC=CC=2)N2CCC1CC2 BIUZWZLMPAUPFK-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 102100024304 Protachykinin-1 Human genes 0.000 description 1
- 101800003906 Substance P Proteins 0.000 description 1
- 230000003474 anti-emetic effect Effects 0.000 description 1
- 239000002111 antiemetic agent Substances 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000002050 diffraction method Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- -1 methyl ethyl Chemical group 0.000 description 1
- 239000013081 microcrystal Substances 0.000 description 1
- 238000000386 microscopy Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 238000001907 polarising light microscopy Methods 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000005062 synaptic transmission Effects 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
- C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/439—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom the ring forming part of a bridged ring system, e.g. quinuclidine
-
- 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
- A61P1/08—Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics
-
- 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
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- 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
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (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)
- Neurosurgery (AREA)
- Hospice & Palliative Care (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Psychiatry (AREA)
- Otolaryngology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US13699599P | 1999-06-01 | 1999-06-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| OA11955A true OA11955A (en) | 2006-04-13 |
Family
ID=22475353
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| OA1200100317A OA11955A (en) | 1999-06-01 | 2000-05-17 | Polymorphs of crystalline (2-benzhydryl-1-azabicycloÄ2-2-2-Üoct-3-yl)-(5-isopropyl-2-methoxybenzyl)-amine citrate as NK-1 receptor antagonists. |
Country Status (38)
| Country | Link |
|---|---|
| US (1) | US6387925B1 (es) |
| EP (1) | EP1181289A1 (es) |
| JP (1) | JP2003501353A (es) |
| KR (1) | KR20020005055A (es) |
| CN (1) | CN1353712A (es) |
| AP (1) | AP2001002350A0 (es) |
| AR (1) | AR029753A1 (es) |
| AU (1) | AU767331B2 (es) |
| BG (1) | BG106139A (es) |
| BR (1) | BR0011125A (es) |
| CA (1) | CA2372236A1 (es) |
| CO (1) | CO5170468A1 (es) |
| CR (1) | CR6513A (es) |
| CZ (1) | CZ20014270A3 (es) |
| DZ (1) | DZ3051A1 (es) |
| EA (1) | EA004206B1 (es) |
| EE (1) | EE200100655A (es) |
| GT (1) | GT200000086A (es) |
| HK (1) | HK1046407A1 (es) |
| HN (1) | HN2000000076A (es) |
| HR (1) | HRP20010884A2 (es) |
| HU (1) | HUP0201798A3 (es) |
| IL (1) | IL145952A0 (es) |
| IS (1) | IS6129A (es) |
| MX (1) | MXPA01012328A (es) |
| NO (1) | NO20015845L (es) |
| NZ (1) | NZ514762A (es) |
| OA (1) | OA11955A (es) |
| PA (1) | PA8496001A1 (es) |
| PE (1) | PE20010155A1 (es) |
| PL (1) | PL352715A1 (es) |
| SK (1) | SK17342001A3 (es) |
| SV (1) | SV2002000092A (es) |
| TN (1) | TNSN00119A1 (es) |
| TR (1) | TR200103472T2 (es) |
| UY (1) | UY26177A1 (es) |
| WO (1) | WO2000073303A1 (es) |
| ZA (1) | ZA200109839B (es) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1551846A1 (en) * | 2002-10-04 | 2005-07-13 | Merck Sharp & Dohme Ltd. | Azabicyclic spiroether derivatives as receptor antagonists |
| KR20070094805A (ko) * | 2003-06-18 | 2007-09-21 | 테바 파마슈티컬 인더스트리즈 리미티드 | 플루바스타틴 나트륨 결정형 ｘｉｖ, ｌｘｘｉｉｉ,ｌｘｘｉｘ, ｌｘｘｘ 및 ｌｘｘｘｖｉｉ, 이의 제조 방법,이를 포함하는 조성물 및 이를 사용하는 방법 |
| US7371906B2 (en) | 2004-08-24 | 2008-05-13 | Eastman Kodak Company | Process for photo-oxidative stability improvements |
| US9446029B2 (en) | 2010-07-27 | 2016-09-20 | Colorado State University Research Foundation | Use of NK-1 receptor antagonists in management of visceral pain |
| CN110577522B (zh) * | 2018-06-07 | 2022-12-27 | 东莞市东阳光动物保健药品有限公司 | 马罗匹坦柠檬酸盐新晶型及其制备方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1990005525A1 (en) * | 1988-11-23 | 1990-05-31 | Pfizer Inc. | Quinuclidine derivatives as substance p antagonists |
| CA2102179C (en) * | 1991-05-31 | 1998-10-27 | Fumitaka Ito | Quinuclidine derivatives |
| US5886009A (en) * | 1992-11-12 | 1999-03-23 | Pfizer Inc. | Quinuclidine derivative as a substance P antagonist |
| US5393762A (en) * | 1993-06-04 | 1995-02-28 | Pfizer Inc. | Pharmaceutical agents for treatment of emesis |
| US6262067B1 (en) * | 1999-06-22 | 2001-07-17 | Pfizer Inc. | Polymorphs of a crystalline azo-bicyclo 2,2,2 OCT-3-yl amine dihydrochloride and their pharmaceutical compositions |
-
2000
- 2000-05-12 US US09/887,682 patent/US6387925B1/en not_active Expired - Fee Related
- 2000-05-17 MX MXPA01012328A patent/MXPA01012328A/es not_active Application Discontinuation
- 2000-05-17 HN HN2000000076A patent/HN2000000076A/es unknown
- 2000-05-17 NZ NZ514762A patent/NZ514762A/xx unknown
- 2000-05-17 BR BR0011125-2A patent/BR0011125A/pt not_active IP Right Cessation
- 2000-05-17 TR TR2001/03472T patent/TR200103472T2/xx unknown
- 2000-05-17 CZ CZ20014270A patent/CZ20014270A3/cs unknown
- 2000-05-17 OA OA1200100317A patent/OA11955A/en unknown
- 2000-05-17 PL PL00352715A patent/PL352715A1/xx not_active Application Discontinuation
- 2000-05-17 SK SK1734-2001A patent/SK17342001A3/sk unknown
- 2000-05-17 EP EP00925526A patent/EP1181289A1/en not_active Withdrawn
- 2000-05-17 AU AU44246/00A patent/AU767331B2/en not_active Ceased
- 2000-05-17 HR HR20010884A patent/HRP20010884A2/hr not_active Application Discontinuation
- 2000-05-17 WO PCT/IB2000/000663 patent/WO2000073303A1/en not_active Ceased
- 2000-05-17 EA EA200100982A patent/EA004206B1/ru not_active IP Right Cessation
- 2000-05-17 CA CA002372236A patent/CA2372236A1/en not_active Abandoned
- 2000-05-17 AP APAP/P/2001/002350A patent/AP2001002350A0/en unknown
- 2000-05-17 JP JP2001500628A patent/JP2003501353A/ja active Pending
- 2000-05-17 HU HU0201798A patent/HUP0201798A3/hu unknown
- 2000-05-17 EE EEP200100655A patent/EE200100655A/xx unknown
- 2000-05-17 HK HK02107840.5A patent/HK1046407A1/zh unknown
- 2000-05-17 CN CN00808340A patent/CN1353712A/zh active Pending
- 2000-05-17 IL IL14595200A patent/IL145952A0/xx unknown
- 2000-05-17 KR KR1020017015324A patent/KR20020005055A/ko not_active Ceased
- 2000-05-19 PA PA20008496001A patent/PA8496001A1/es unknown
- 2000-05-26 CO CO00039192A patent/CO5170468A1/es not_active Application Discontinuation
- 2000-05-29 UY UY26177A patent/UY26177A1/es not_active Application Discontinuation
- 2000-05-30 GT GT200000086A patent/GT200000086A/es unknown
- 2000-05-30 AR ARP000102664A patent/AR029753A1/es unknown
- 2000-05-30 PE PE2000000517A patent/PE20010155A1/es not_active Application Discontinuation
- 2000-05-31 SV SV2000000092A patent/SV2002000092A/es unknown
- 2000-05-31 TN TNTNSN00119A patent/TNSN00119A1/fr unknown
- 2000-05-31 DZ DZ000102A patent/DZ3051A1/xx active
-
2001
- 2001-10-26 IS IS6129A patent/IS6129A/is unknown
- 2001-11-23 BG BG106139A patent/BG106139A/bg unknown
- 2001-11-27 CR CR6513A patent/CR6513A/es not_active Application Discontinuation
- 2001-11-29 ZA ZA200109839A patent/ZA200109839B/xx unknown
- 2001-11-30 NO NO20015845A patent/NO20015845L/no not_active Application Discontinuation
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