CA2789884A1 - Solid forms comprising a cyclopropyl amide derivative - Google Patents
Solid forms comprising a cyclopropyl amide derivative Download PDFInfo
- Publication number
- CA2789884A1 CA2789884A1 CA2789884A CA2789884A CA2789884A1 CA 2789884 A1 CA2789884 A1 CA 2789884A1 CA 2789884 A CA2789884 A CA 2789884A CA 2789884 A CA2789884 A CA 2789884A CA 2789884 A1 CA2789884 A1 CA 2789884A1
- Authority
- CA
- Canada
- Prior art keywords
- compound
- solid form
- disorder
- schizophrenia
- solid
- 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
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- 239000007787 solid Substances 0.000 title claims abstract description 106
- HTJDQJBWANPRPF-UHFFFAOYSA-N Cyclopropylamine Chemical class NC1CC1 HTJDQJBWANPRPF-UHFFFAOYSA-N 0.000 title description 2
- 238000000034 method Methods 0.000 claims abstract description 65
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 27
- 238000004519 manufacturing process Methods 0.000 claims abstract description 16
- 150000001875 compounds Chemical class 0.000 claims description 167
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 49
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 40
- 208000035475 disorder Diseases 0.000 claims description 39
- 241001465754 Metazoa Species 0.000 claims description 38
- 230000036407 pain Effects 0.000 claims description 33
- 201000000980 schizophrenia Diseases 0.000 claims description 33
- 208000002193 Pain Diseases 0.000 claims description 29
- 208000024827 Alzheimer disease Diseases 0.000 claims description 28
- 238000011282 treatment Methods 0.000 claims description 28
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims description 26
- 208000008589 Obesity Diseases 0.000 claims description 26
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims description 24
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims description 24
- 235000020824 obesity Nutrition 0.000 claims description 24
- 230000005855 radiation Effects 0.000 claims description 24
- 230000019771 cognition Effects 0.000 claims description 23
- 238000002560 therapeutic procedure Methods 0.000 claims description 23
- 230000007812 deficiency Effects 0.000 claims description 20
- 201000003631 narcolepsy Diseases 0.000 claims description 20
- 239000003814 drug Substances 0.000 claims description 18
- 208000007590 Disorders of Excessive Somnolence Diseases 0.000 claims description 14
- 206010041349 Somnolence Diseases 0.000 claims description 14
- 239000003937 drug carrier Substances 0.000 claims description 11
- 239000003085 diluting agent Substances 0.000 claims description 9
- 238000001757 thermogravimetry curve Methods 0.000 claims description 9
- 238000001938 differential scanning calorimetry curve Methods 0.000 claims description 8
- 230000008569 process Effects 0.000 abstract description 11
- NJJBLDDRYMCIMQ-XWIAVFTESA-N 4-[(1s,2s)-2-[(2r)-4-cyclobutyl-2-methylpiperazine-1-carbonyl]cyclopropyl]benzamide Chemical compound C1([C@H]2C[C@@H]2C(=O)N2CCN(C[C@H]2C)C2CCC2)=CC=C(C(N)=O)C=C1 NJJBLDDRYMCIMQ-XWIAVFTESA-N 0.000 abstract description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 75
- 229910001868 water Inorganic materials 0.000 description 73
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 71
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 47
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 42
- 239000012071 phase Substances 0.000 description 41
- 239000000243 solution Substances 0.000 description 41
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 38
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical class ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
- 238000001228 spectrum Methods 0.000 description 36
- 239000000203 mixture Substances 0.000 description 34
- 230000001747 exhibiting effect Effects 0.000 description 32
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 26
- 238000004458 analytical method Methods 0.000 description 26
- 238000005079 FT-Raman Methods 0.000 description 25
- 238000006243 chemical reaction Methods 0.000 description 25
- 239000011541 reaction mixture Substances 0.000 description 25
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 22
- 238000005160 1H NMR spectroscopy Methods 0.000 description 21
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 20
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 description 19
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 19
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 19
- 239000000047 product Substances 0.000 description 19
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- -1 C1.6-alkyl acetates Chemical class 0.000 description 17
- 239000002207 metabolite Substances 0.000 description 17
- 239000012074 organic phase Substances 0.000 description 17
- 238000003756 stirring Methods 0.000 description 17
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 16
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 15
- 239000002245 particle Substances 0.000 description 15
- 238000001157 Fourier transform infrared spectrum Methods 0.000 description 14
- 238000000113 differential scanning calorimetry Methods 0.000 description 14
- 238000004949 mass spectrometry Methods 0.000 description 14
- 230000007278 cognition impairment Effects 0.000 description 13
- 238000004128 high performance liquid chromatography Methods 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 11
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 10
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 10
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
- 238000005384 cross polarization magic-angle spinning Methods 0.000 description 10
- 229960004592 isopropanol Drugs 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 9
- 208000027753 pain disease Diseases 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- 238000002411 thermogravimetry Methods 0.000 description 9
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 8
- 206010012289 Dementia Diseases 0.000 description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- 102000004384 Histamine H3 receptors Human genes 0.000 description 8
- 108090000981 Histamine H3 receptors Proteins 0.000 description 8
- 229940079593 drug Drugs 0.000 description 8
- 238000001035 drying Methods 0.000 description 8
- 235000019253 formic acid Nutrition 0.000 description 8
- 239000003112 inhibitor Substances 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 239000005557 antagonist Substances 0.000 description 7
- 239000012267 brine Substances 0.000 description 7
- 235000019341 magnesium sulphate Nutrition 0.000 description 7
- 239000002002 slurry Substances 0.000 description 7
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 7
- 238000003860 storage Methods 0.000 description 7
- 238000000825 ultraviolet detection Methods 0.000 description 7
- 101150041968 CDC13 gene Proteins 0.000 description 6
- UGJMXCAKCUNAIE-UHFFFAOYSA-N Gabapentin Chemical compound OC(=O)CC1(CN)CCCCC1 UGJMXCAKCUNAIE-UHFFFAOYSA-N 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
- 239000008186 active pharmaceutical agent Substances 0.000 description 6
- 230000037396 body weight Effects 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 208000010877 cognitive disease Diseases 0.000 description 6
- 229940088679 drug related substance Drugs 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 235000011007 phosphoric acid Nutrition 0.000 description 6
- 208000020016 psychiatric disease Diseases 0.000 description 6
- 238000000746 purification Methods 0.000 description 6
- 239000012066 reaction slurry Substances 0.000 description 6
- 239000011343 solid material Substances 0.000 description 6
- 208000030814 Eating disease Diseases 0.000 description 5
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 5
- 238000005481 NMR spectroscopy Methods 0.000 description 5
- 235000019270 ammonium chloride Nutrition 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 238000004896 high resolution mass spectrometry Methods 0.000 description 5
- 208000024714 major depressive disease Diseases 0.000 description 5
- 201000006417 multiple sclerosis Diseases 0.000 description 5
- DAZXVJBJRMWXJP-UHFFFAOYSA-N n,n-dimethylethylamine Chemical compound CCN(C)C DAZXVJBJRMWXJP-UHFFFAOYSA-N 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- 208000004296 neuralgia Diseases 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 229940075993 receptor modulator Drugs 0.000 description 5
- 239000000377 silicon dioxide Substances 0.000 description 5
- 235000017557 sodium bicarbonate Nutrition 0.000 description 5
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
- 238000004611 spectroscopical analysis Methods 0.000 description 5
- 238000004808 supercritical fluid chromatography Methods 0.000 description 5
- 230000004580 weight loss Effects 0.000 description 5
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 4
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 4
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 4
- 208000027448 Attention Deficit and Disruptive Behavior disease Diseases 0.000 description 4
- 208000023275 Autoimmune disease Diseases 0.000 description 4
- 208000020925 Bipolar disease Diseases 0.000 description 4
- 208000030939 Chronic inflammatory demyelinating polyneuropathy Diseases 0.000 description 4
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 4
- 208000019454 Feeding and Eating disease Diseases 0.000 description 4
- 201000011240 Frontotemporal dementia Diseases 0.000 description 4
- 208000035895 Guillain-Barré syndrome Diseases 0.000 description 4
- 206010049567 Miller Fisher syndrome Diseases 0.000 description 4
- 208000019022 Mood disease Diseases 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 208000018737 Parkinson disease Diseases 0.000 description 4
- 208000028017 Psychotic disease Diseases 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 235000011114 ammonium hydroxide Nutrition 0.000 description 4
- 201000005795 chronic inflammatory demyelinating polyneuritis Diseases 0.000 description 4
- 208000007118 chronic progressive multiple sclerosis Diseases 0.000 description 4
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- 239000013078 crystal Substances 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 235000014632 disordered eating Nutrition 0.000 description 4
- 238000003818 flash chromatography Methods 0.000 description 4
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 4
- 208000035231 inattentive type attention deficit hyperactivity disease Diseases 0.000 description 4
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 4
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- MSRILKIQRXUYCT-UHFFFAOYSA-M valproate semisodium Chemical compound [Na+].CCCC(C(O)=O)CCC.CCCC(C([O-])=O)CCC MSRILKIQRXUYCT-UHFFFAOYSA-M 0.000 description 4
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- ZEUITGRIYCTCEM-KRWDZBQOSA-N (S)-duloxetine Chemical compound C1([C@@H](OC=2C3=CC=CC=C3C=CC=2)CCNC)=CC=CS1 ZEUITGRIYCTCEM-KRWDZBQOSA-N 0.000 description 3
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 3
- HCQNNQFCUAGJBD-UHFFFAOYSA-N 1-(4-bromophenyl)-2-chloroethanone Chemical compound ClCC(=O)C1=CC=C(Br)C=C1 HCQNNQFCUAGJBD-UHFFFAOYSA-N 0.000 description 3
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 3
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 3
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- AEQFSUDEHCCHBT-UHFFFAOYSA-M sodium valproate Chemical compound [Na+].CCCC(C([O-])=O)CCC AEQFSUDEHCCHBT-UHFFFAOYSA-M 0.000 description 3
- 238000001179 sorption measurement Methods 0.000 description 3
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- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 3
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- KWGRBVOPPLSCSI-WPRPVWTQSA-N (-)-ephedrine Chemical compound CN[C@@H](C)[C@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WPRPVWTQSA-N 0.000 description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/192—Radicals derived from carboxylic acids from aromatic carboxylic acids
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
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- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
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- 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
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- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- 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
- A61P25/28—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
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/04—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Epidemiology (AREA)
- Psychiatry (AREA)
- Hospice & Palliative Care (AREA)
- Child & Adolescent Psychology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US30558110P | 2010-02-18 | 2010-02-18 | |
| US61/305,581 | 2010-02-18 | ||
| PCT/SE2011/050170 WO2011102793A1 (en) | 2010-02-18 | 2011-02-17 | Solid forms comprising a cyclopropyl amide derivative |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2789884A1 true CA2789884A1 (en) | 2011-08-25 |
Family
ID=44370079
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2789884A Abandoned CA2789884A1 (en) | 2010-02-18 | 2011-02-17 | Solid forms comprising a cyclopropyl amide derivative |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US20110201622A1 (enExample) |
| EP (1) | EP2536701A4 (enExample) |
| JP (1) | JP5746718B2 (enExample) |
| KR (1) | KR20130034009A (enExample) |
| CN (1) | CN103140481A (enExample) |
| AR (1) | AR080203A1 (enExample) |
| AU (1) | AU2011218490B9 (enExample) |
| BR (1) | BR112012020780A2 (enExample) |
| CA (1) | CA2789884A1 (enExample) |
| CL (1) | CL2012002285A1 (enExample) |
| IL (1) | IL221430A0 (enExample) |
| MX (1) | MX2012009537A (enExample) |
| NZ (1) | NZ602108A (enExample) |
| RU (1) | RU2012136921A (enExample) |
| SG (1) | SG183231A1 (enExample) |
| TW (1) | TW201136898A (enExample) |
| WO (1) | WO2011102793A1 (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| UA101809C2 (uk) | 2007-08-22 | 2013-05-13 | Астразенека Аб | Похідні циклопропіламіду |
| TW201039825A (en) * | 2009-02-20 | 2010-11-16 | Astrazeneca Ab | Cyclopropyl amide derivatives 983 |
| KR20130002316A (ko) * | 2010-02-18 | 2013-01-07 | 아스트라제네카 아베 | 시클로프로필 벤즈아미드 유도체의 신규 결정질 형태 |
| CN109438423A (zh) * | 2018-09-12 | 2019-03-08 | 通化师范学院 | 一种肺癌靶向化合物azd-3759的合成工艺的新方法 |
Family Cites Families (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE637271A (enExample) * | 1963-04-04 | 1900-01-01 | ||
| US3449427A (en) * | 1965-06-03 | 1969-06-10 | Smithkline Corp | Aminocyclopropane derivatives of 5h-dibenzo(a,d)cycloheptenes |
| US3697506A (en) * | 1970-08-07 | 1972-10-10 | Pfizer | Crystalline alkali metal salts of {60 -carboxybenzylpenicillin and process therefor |
| US3686335A (en) * | 1970-12-21 | 1972-08-22 | Smith Kline French Lab | 5-vinyl-5h-di benzo(a,d)cycloheptenes |
| US4432987A (en) * | 1982-04-23 | 1984-02-21 | Pfizer Inc. | Crystalline benzenesulfonate salts of sultamicillin |
| US4547505A (en) * | 1983-03-25 | 1985-10-15 | Degussa Aktiengesellschaft | N-Phenyl-N-'-cycloalkylalkanoylpiperazine useful as analgetics and process for its production |
| CA2033390A1 (en) * | 1989-12-29 | 1991-06-30 | Susumu Nakagawa | 2-(2-cyclopropylpyrrolidin-4-ylthio) carbapenem derivatives |
| DE4131139A1 (de) * | 1991-09-19 | 1993-03-25 | Bayer Ag | Verfahren zur herstellung von 1-fluor-cyclopropan-1-carbonsaeure |
| HU222244B1 (hu) * | 1993-03-12 | 2003-05-28 | Pharmacia & Upjohn Co. | Szabad sav formájában lévő kristályos ceftiofur, ennek előállítása és ezt tartalmazó gyógyászati készítmény |
| AU4531499A (en) * | 1998-06-26 | 2000-01-17 | Chugai Seiyaku Kabushiki Kaisha | Fine powder of l-alpha-aminoadipic acid derivative, oral solid preparations containing the same, and method for treatment of bulk powders |
| US6284761B1 (en) * | 1999-01-08 | 2001-09-04 | Neurogen Corporation | 1-phenyl-4-(1-[2-aryl]cyclopropyl)methylpiperazines: dopamine receptor ligands |
| SK9742002A3 (en) * | 2000-01-07 | 2003-02-04 | Transform Pharmaceuticals Inc | High-throughput formation, identification, and analysis of diverse solid-forms |
| US6521619B2 (en) * | 2000-06-29 | 2003-02-18 | Icos Corporation | Aryl phenylcyclopropyl sulfide derivatives and their use as cell adhesion inhibiting anti-inflammatory and immune suppressive agents |
| HUP0303258A3 (en) * | 2001-02-23 | 2004-06-28 | Merck & Co Inc | N-substituted nonaryl-heterocyclic nmda/nr2b antagonists and pharmaceutical compositions containing them |
| CA2457642C (en) * | 2001-09-26 | 2009-01-06 | Merck & Co., Inc. | Crystalline forms of ertapenem sodium |
| US6861432B2 (en) * | 2001-11-23 | 2005-03-01 | Schering Aktiengesellschaft | Piperazine derivatives that destabilize androgen receptors |
| RU2004131204A (ru) * | 2002-03-22 | 2005-04-10 | Эл Джи Лайф Сайенсиз Лтд. (Kr) | НОВЫЕ КРИСТАЛЛИЧЕСКИЕ ФОРМЫ (2S)-N-5-[АМИНО(ИМИНО)МЕТИЛ]-2-ТИЕНИЛМЕТИЛ-1-(2R)- [(КАРБОКСИМЕТИЛ)АМИНО]-3 ,3-Д ИФЕНИЛПРОПАНОИЛ-2-ПИРРОЛИДИНКАРБОКСАМИДА·nH2O |
| US20040209858A1 (en) * | 2002-10-22 | 2004-10-21 | Bennani Youssef L. | Cycloalkylamides and their therapeutic applications |
| US20040077618A1 (en) * | 2002-10-22 | 2004-04-22 | Bennani Youssef L. | Cycloalkylamides and their therapeutic applications |
| JP2006528939A (ja) * | 2003-04-23 | 2006-12-28 | グラクソ グループ リミテッド | ピペラジン誘導体ならびに神経および精神疾患の治療のためのその使用 |
| TWI339206B (en) * | 2003-09-04 | 2011-03-21 | Vertex Pharma | Compositions useful as inhibitors of protein kinases |
| UA96424C2 (ru) * | 2005-09-16 | 2011-11-10 | Янссен Фармацевтика Н.В. | Циклопропил амины как модуляторы н3 рецепторов гистамина |
| WO2007080140A1 (en) * | 2006-01-13 | 2007-07-19 | F. Hoffmann-La Roche Ag | Cyclohexyl piperazinyl methanone derivatives and their use as histamine h3 receptor modulators |
| US9108948B2 (en) * | 2006-06-23 | 2015-08-18 | Abbvie Inc. | Cyclopropyl amine derivatives |
| US8829041B2 (en) * | 2006-06-23 | 2014-09-09 | Abbvie Inc. | Cyclopropyl amine derivatives |
| TW200828371A (en) * | 2006-09-21 | 2008-07-01 | Matsushita Electric Industrial Co Ltd | Chip-type filter |
| UA101809C2 (uk) * | 2007-08-22 | 2013-05-13 | Астразенека Аб | Похідні циклопропіламіду |
| WO2009043784A1 (en) * | 2007-10-04 | 2009-04-09 | F. Hoffmann-La Roche Ag | Cyclopropyl aryl amide derivatives and uses thereof |
| AR070107A1 (es) * | 2008-01-15 | 2010-03-17 | Lilly Co Eli | R-2-(4-ciclopropansulfonil-fenil)-n-pirazin-2-il-3-(tetrahidropiran-4-il)-propionamida en forma cristalina, composicion farmaceutica que la comprende y su uso para la manufactura de un medicamento util para la prevencion o tratamiento de hiperglicemia |
| TW201039825A (en) * | 2009-02-20 | 2010-11-16 | Astrazeneca Ab | Cyclopropyl amide derivatives 983 |
| KR20130002316A (ko) * | 2010-02-18 | 2013-01-07 | 아스트라제네카 아베 | 시클로프로필 벤즈아미드 유도체의 신규 결정질 형태 |
-
2011
- 2011-02-17 AR ARP110100484A patent/AR080203A1/es unknown
- 2011-02-17 BR BR112012020780A patent/BR112012020780A2/pt not_active IP Right Cessation
- 2011-02-17 CA CA2789884A patent/CA2789884A1/en not_active Abandoned
- 2011-02-17 TW TW100105298A patent/TW201136898A/zh unknown
- 2011-02-17 SG SG2012058848A patent/SG183231A1/en unknown
- 2011-02-17 NZ NZ602108A patent/NZ602108A/en not_active IP Right Cessation
- 2011-02-17 EP EP20110744973 patent/EP2536701A4/en not_active Withdrawn
- 2011-02-17 AU AU2011218490A patent/AU2011218490B9/en not_active Ceased
- 2011-02-17 US US13/029,351 patent/US20110201622A1/en not_active Abandoned
- 2011-02-17 MX MX2012009537A patent/MX2012009537A/es not_active Application Discontinuation
- 2011-02-17 JP JP2012553848A patent/JP5746718B2/ja not_active Expired - Fee Related
- 2011-02-17 KR KR1020127024173A patent/KR20130034009A/ko not_active Withdrawn
- 2011-02-17 CN CN201180019676XA patent/CN103140481A/zh active Pending
- 2011-02-17 WO PCT/SE2011/050170 patent/WO2011102793A1/en not_active Ceased
- 2011-02-17 RU RU2012136921/04A patent/RU2012136921A/ru not_active Application Discontinuation
-
2012
- 2012-08-13 IL IL221430A patent/IL221430A0/en unknown
- 2012-08-17 CL CL2012002285A patent/CL2012002285A1/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CN103140481A (zh) | 2013-06-05 |
| BR112012020780A2 (pt) | 2016-05-03 |
| TW201136898A (en) | 2011-11-01 |
| WO2011102793A1 (en) | 2011-08-25 |
| US20110201622A1 (en) | 2011-08-18 |
| MX2012009537A (es) | 2012-08-31 |
| RU2012136921A (ru) | 2014-03-27 |
| EP2536701A4 (en) | 2014-05-07 |
| KR20130034009A (ko) | 2013-04-04 |
| SG183231A1 (en) | 2012-09-27 |
| EP2536701A1 (en) | 2012-12-26 |
| JP2013520412A (ja) | 2013-06-06 |
| JP5746718B2 (ja) | 2015-07-08 |
| AU2011218490B2 (en) | 2014-11-13 |
| IL221430A0 (en) | 2012-10-31 |
| CL2012002285A1 (es) | 2013-01-25 |
| AR080203A1 (es) | 2012-03-21 |
| AU2011218490B9 (en) | 2014-12-18 |
| NZ602108A (en) | 2014-09-26 |
| AU2011218490A1 (en) | 2012-10-04 |
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Legal Events
| Date | Code | Title | Description |
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| FZDE | Discontinued |
Effective date: 20170217 |