ES2745080T3 - Cocristales de compuestos de bencimidazol - Google Patents
Cocristales de compuestos de bencimidazol Download PDFInfo
- Publication number
- ES2745080T3 ES2745080T3 ES16797941T ES16797941T ES2745080T3 ES 2745080 T3 ES2745080 T3 ES 2745080T3 ES 16797941 T ES16797941 T ES 16797941T ES 16797941 T ES16797941 T ES 16797941T ES 2745080 T3 ES2745080 T3 ES 2745080T3
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- Prior art keywords
- crystal
- bilastine
- acid
- molar ratio
- water
- Prior art date
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- 239000013078 crystal Substances 0.000 title claims abstract description 225
- -1 Benzimidazole compound Chemical class 0.000 title description 6
- ACCMWZWAEFYUGZ-UHFFFAOYSA-N bilastine Chemical compound N=1C2=CC=CC=C2N(CCOCC)C=1C(CC1)CCN1CCC1=CC=C(C(C)(C)C(O)=O)C=C1 ACCMWZWAEFYUGZ-UHFFFAOYSA-N 0.000 claims abstract description 205
- 229960004314 bilastine Drugs 0.000 claims abstract description 204
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims abstract description 58
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims abstract description 57
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims abstract description 42
- 239000000203 mixture Substances 0.000 claims abstract description 40
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 claims abstract description 38
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 claims abstract description 35
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 claims abstract description 34
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims abstract description 34
- 150000001875 compounds Chemical class 0.000 claims abstract description 33
- 239000005711 Benzoic acid Substances 0.000 claims abstract description 30
- 235000010233 benzoic acid Nutrition 0.000 claims abstract description 30
- 239000001361 adipic acid Substances 0.000 claims abstract description 29
- 235000011037 adipic acid Nutrition 0.000 claims abstract description 29
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 claims abstract description 22
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 claims abstract description 21
- 239000004334 sorbic acid Substances 0.000 claims abstract description 21
- 229940075582 sorbic acid Drugs 0.000 claims abstract description 21
- 235000010199 sorbic acid Nutrition 0.000 claims abstract description 21
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 claims abstract description 19
- 235000011090 malic acid Nutrition 0.000 claims abstract description 19
- 229940116298 l- malic acid Drugs 0.000 claims abstract description 15
- 239000012453 solvate Substances 0.000 claims abstract description 14
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 claims abstract description 11
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 claims abstract description 10
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims abstract description 6
- 229960000250 adipic acid Drugs 0.000 claims abstract description 5
- ALYNCZNDIQEVRV-PZFLKRBQSA-N 4-amino-3,5-ditritiobenzoic acid Chemical compound [3H]c1cc(cc([3H])c1N)C(O)=O ALYNCZNDIQEVRV-PZFLKRBQSA-N 0.000 claims abstract description 4
- 229960004365 benzoic acid Drugs 0.000 claims abstract description 4
- 229960001755 resorcinol Drugs 0.000 claims abstract description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 72
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 42
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 42
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 claims description 40
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 38
- 239000002904 solvent Substances 0.000 claims description 27
- 230000007935 neutral effect Effects 0.000 claims description 26
- 238000000034 method Methods 0.000 claims description 21
- 229960004050 aminobenzoic acid Drugs 0.000 claims description 20
- 238000003756 stirring Methods 0.000 claims description 20
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 18
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 18
- 239000001384 succinic acid Substances 0.000 claims description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 13
- 239000008194 pharmaceutical composition Substances 0.000 claims description 13
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 10
- 208000026935 allergic disease Diseases 0.000 claims description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 8
- 206010010741 Conjunctivitis Diseases 0.000 claims description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 8
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
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- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 4
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 4
- 208000024780 Urticaria Diseases 0.000 claims description 4
- 208000006673 asthma Diseases 0.000 claims description 4
- 238000001816 cooling Methods 0.000 claims description 4
- 206010039083 rhinitis Diseases 0.000 claims description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 2
- 201000004624 Dermatitis Diseases 0.000 claims description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 2
- GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 claims description 2
- FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 claims description 2
- OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 claims description 2
- 239000008096 xylene Substances 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 47
- 238000000634 powder X-ray diffraction Methods 0.000 description 45
- 239000007787 solid Substances 0.000 description 44
- 239000000725 suspension Substances 0.000 description 29
- 238000001914 filtration Methods 0.000 description 21
- 125000001931 aliphatic group Chemical group 0.000 description 20
- 238000004458 analytical method Methods 0.000 description 18
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 13
- 238000012512 characterization method Methods 0.000 description 10
- 201000010099 disease Diseases 0.000 description 9
- 229920006395 saturated elastomer Polymers 0.000 description 9
- 150000001556 benzimidazoles Chemical class 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 8
- 125000000217 alkyl group Chemical group 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 125000000524 functional group Chemical group 0.000 description 7
- 230000008569 process Effects 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 6
- GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 6
- 230000003993 interaction Effects 0.000 description 6
- 125000001424 substituent group Chemical group 0.000 description 6
- 238000001238 wet grinding Methods 0.000 description 6
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 5
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 5
- 239000000739 antihistaminic agent Substances 0.000 description 5
- 150000004677 hydrates Chemical class 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 230000002378 acidificating effect Effects 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 230000001387 anti-histamine Effects 0.000 description 4
- 150000001558 benzoic acid derivatives Chemical group 0.000 description 4
- 238000013480 data collection Methods 0.000 description 4
- 239000001630 malic acid Substances 0.000 description 4
- 229940099690 malic acid Drugs 0.000 description 4
- 238000010899 nucleation Methods 0.000 description 4
- 150000002989 phenols Chemical class 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
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- 206010010744 Conjunctivitis allergic Diseases 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- 230000008485 antagonism Effects 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 208000035475 disorder Diseases 0.000 description 3
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- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- FJKROLUGYXJWQN-UHFFFAOYSA-M 4-hydroxybenzoate Chemical compound OC1=CC=C(C([O-])=O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-M 0.000 description 2
- 102000003834 Histamine H1 Receptors Human genes 0.000 description 2
- 108090000110 Histamine H1 Receptors Proteins 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 201000010435 allergic urticaria Diseases 0.000 description 2
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 238000010908 decantation Methods 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 235000019439 ethyl acetate Nutrition 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 238000007911 parenteral administration Methods 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 102000005962 receptors Human genes 0.000 description 2
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- 238000009331 sowing Methods 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 208000024891 symptom Diseases 0.000 description 2
- 238000003828 vacuum filtration Methods 0.000 description 2
- 239000003981 vehicle Substances 0.000 description 2
- ZTMADXFOCUXMJE-UHFFFAOYSA-N 2-methylbenzene-1,3-diol Chemical compound CC1=C(O)C=CC=C1O ZTMADXFOCUXMJE-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
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- 238000001157 Fourier transform infrared spectrum Methods 0.000 description 1
- 208000012895 Gastric disease Diseases 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 102000000543 Histamine Receptors Human genes 0.000 description 1
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- 206010020751 Hypersensitivity Diseases 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 206010039085 Rhinitis allergic Diseases 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
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- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
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- 239000008121 dextrose Substances 0.000 description 1
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- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- ASHGTJPOSUFTGB-UHFFFAOYSA-N methyl resorcinol Natural products COC1=CC=CC(O)=C1 ASHGTJPOSUFTGB-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/02—Nasal agents, e.g. decongestants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
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- A—HUMAN NECESSITIES
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- A61P17/00—Drugs for dermatological disorders
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61P17/04—Antipruritics
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- A—HUMAN NECESSITIES
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- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/52—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
- C07C229/54—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton with amino and carboxyl groups bound to carbon atoms of the same non-condensed six-membered aromatic ring
- C07C229/60—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton with amino and carboxyl groups bound to carbon atoms of the same non-condensed six-membered aromatic ring with amino and carboxyl groups bound in meta- or para- positions
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/32—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
- C07C235/34—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
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- C—CHEMISTRY; METALLURGY
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- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/02—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring monocyclic with no unsaturation outside the aromatic ring
- C07C39/10—Polyhydroxy benzenes; Alkylated derivatives thereof
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- C07C55/00—Saturated compounds having more than one carboxyl group bound to acyclic carbon atoms
- C07C55/02—Dicarboxylic acids
- C07C55/10—Succinic acid
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- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
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- C07C63/00—Compounds having carboxyl groups bound to a carbon atoms of six-membered aromatic rings
- C07C63/04—Monocyclic monocarboxylic acids
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- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
- C07C69/84—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring
- C07C69/88—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring with esterified carboxyl groups
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- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
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- Immunology (AREA)
- Ophthalmology & Optometry (AREA)
- Otolaryngology (AREA)
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- Plural Heterocyclic Compounds (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP15382577.3A EP3170817A1 (en) | 2015-11-20 | 2015-11-20 | Co-crystals of benzimidazole compounds |
| PCT/EP2016/078145 WO2017085258A1 (en) | 2015-11-20 | 2016-11-18 | Co-crystals of benzimidazole compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2745080T3 true ES2745080T3 (es) | 2020-02-27 |
Family
ID=54707731
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES16797941T Active ES2745080T3 (es) | 2015-11-20 | 2016-11-18 | Cocristales de compuestos de bencimidazol |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US20180319766A1 (enExample) |
| EP (2) | EP3170817A1 (enExample) |
| JP (1) | JP2018535223A (enExample) |
| CN (1) | CN108290857A (enExample) |
| BR (1) | BR112018010276A2 (enExample) |
| CA (1) | CA3005387A1 (enExample) |
| EA (1) | EA201891168A1 (enExample) |
| ES (1) | ES2745080T3 (enExample) |
| MX (1) | MX2018006252A (enExample) |
| PT (1) | PT3377478T (enExample) |
| WO (1) | WO2017085258A1 (enExample) |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2048109B1 (es) | 1992-07-20 | 1994-12-16 | Espanola Prod Quimicos | Procedimiento de preparacion de nuevos derivados piperidicos del bencimidazol. |
| ES2124167B1 (es) | 1996-06-04 | 1999-09-16 | Espanola Prod Quimicos | Nuevos derivados del bencimidazol con actividad antihistaminica. |
| ATE347550T1 (de) * | 2002-04-19 | 2006-12-15 | Faes Farma Sa | Polymorph von 4-(2-(4-(1-(2-ethoxyethyl)-1h- benzimidazol-2-yl)-1-piperidinyl)ethyl)-alpha, alpha-dimethylbenzolessigsäure |
| WO2008054609A2 (en) * | 2006-10-04 | 2008-05-08 | The Regents Of The University Of Michigan | Dissolution and precipitation of cocrystals with ionizable components |
| TWI580442B (zh) * | 2011-10-19 | 2017-05-01 | 傑特大學 | 醫藥毫微懸浮物 |
| CN103351380B (zh) * | 2013-06-30 | 2019-01-22 | 北京万全德众医药生物技术有限公司 | 一种制备比拉斯汀的方法 |
| SK7066Y1 (sk) | 2014-01-29 | 2015-03-03 | Zentiva Ks | Kryštalický dihydrát bilastínu |
| CN103788062A (zh) | 2014-02-17 | 2014-05-14 | 北京博泽德润医药科技开发有限公司 | 一种比拉斯汀晶型及其制备方法 |
-
2015
- 2015-11-20 EP EP15382577.3A patent/EP3170817A1/en not_active Withdrawn
-
2016
- 2016-11-18 ES ES16797941T patent/ES2745080T3/es active Active
- 2016-11-18 MX MX2018006252A patent/MX2018006252A/es unknown
- 2016-11-18 US US15/775,831 patent/US20180319766A1/en not_active Abandoned
- 2016-11-18 CA CA3005387A patent/CA3005387A1/en not_active Abandoned
- 2016-11-18 BR BR112018010276A patent/BR112018010276A2/pt not_active Application Discontinuation
- 2016-11-18 CN CN201680067635.0A patent/CN108290857A/zh active Pending
- 2016-11-18 EA EA201891168A patent/EA201891168A1/ru unknown
- 2016-11-18 EP EP16797941.8A patent/EP3377478B1/en active Active
- 2016-11-18 JP JP2018526145A patent/JP2018535223A/ja not_active Withdrawn
- 2016-11-18 PT PT167979418T patent/PT3377478T/pt unknown
- 2016-11-18 WO PCT/EP2016/078145 patent/WO2017085258A1/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| BR112018010276A2 (pt) | 2018-11-27 |
| CA3005387A1 (en) | 2017-05-26 |
| EP3170817A1 (en) | 2017-05-24 |
| JP2018535223A (ja) | 2018-11-29 |
| MX2018006252A (es) | 2019-04-04 |
| WO2017085258A1 (en) | 2017-05-26 |
| US20180319766A1 (en) | 2018-11-08 |
| EP3377478A1 (en) | 2018-09-26 |
| EA201891168A1 (ru) | 2018-11-30 |
| CN108290857A (zh) | 2018-07-17 |
| PT3377478T (pt) | 2019-10-11 |
| EP3377478B1 (en) | 2019-07-24 |
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