HUE034929T2 - Heterocyclic compounds, medicaments containing said compounds, use thereof and processes for the preparation thereof - Google Patents

Info

Publication number

HUE034929T2

HUE034929T2 HUE12777930A HUE12777930A HUE034929T2 HU E034929 T2 HUE034929 T2 HU E034929T2 HU E12777930 A HUE12777930 A HU E12777930A HU E12777930 A HUE12777930 A HU E12777930A HU E034929 T2 HUE034929 T2 HU E034929T2

Authority

HU

Hungary

Prior art keywords

alkyl

ója

phenyl

amino

acid

Prior art date

2011-11-02

Links

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• Global Dossier
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• 150000001875 compounds Chemical class 0.000 title claims abstract description 163
• 238000000034 method Methods 0.000 title description 53
• 239000003814 drug Substances 0.000 title description 9
• 238000002360 preparation method Methods 0.000 title description 7
• 150000002391 heterocyclic compounds Chemical class 0.000 title 1
• 150000003839 salts Chemical class 0.000 claims abstract description 94
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 25
• 201000010099 disease Diseases 0.000 claims abstract description 21
• 239000002253 acid Substances 0.000 claims description 80
• 239000000203 mixture Substances 0.000 claims description 65
• 206010006451 bronchitis Diseases 0.000 claims description 34
• 239000002904 solvent Substances 0.000 claims description 24
• 239000000126 substance Substances 0.000 claims description 23
• 239000003112 inhibitor Substances 0.000 claims description 14
• 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 12
• 230000000172 allergic effect Effects 0.000 claims description 12
• 208000006673 asthma Diseases 0.000 claims description 12
• 229910052739 hydrogen Inorganic materials 0.000 claims description 12
• 239000001257 hydrogen Substances 0.000 claims description 11
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 10
• 206010001889 Alveolitis Diseases 0.000 claims description 8
• 208000010668 atopic eczema Diseases 0.000 claims description 8
• 201000001155 extrinsic allergic alveolitis Diseases 0.000 claims description 8
• 208000022098 hypersensitivity pneumonitis Diseases 0.000 claims description 8
• 230000001684 chronic effect Effects 0.000 claims description 7
• 229910052757 nitrogen Inorganic materials 0.000 claims description 7
• 239000008194 pharmaceutical composition Substances 0.000 claims description 6
• 206010011224 Cough Diseases 0.000 claims description 5
• 241000233866 Fungi Species 0.000 claims description 5
• 206010039085 Rhinitis allergic Diseases 0.000 claims description 5
• 239000000808 adrenergic beta-agonist Substances 0.000 claims description 5
• 201000010105 allergic rhinitis Diseases 0.000 claims description 5
• 230000003454 betamimetic effect Effects 0.000 claims description 5
• 239000002713 epithelial sodium channel blocking agent Substances 0.000 claims description 5
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 5
• 206010052613 Allergic bronchitis Diseases 0.000 claims description 4
• 125000000217 alkyl group Chemical group 0.000 claims description 4
• 208000029771 childhood onset asthma Diseases 0.000 claims description 4
• 208000036142 Viral infection Diseases 0.000 claims description 3
• 239000004094 surface-active agent Substances 0.000 claims description 3
• 231100000331 toxic Toxicity 0.000 claims description 3
• 230000002588 toxic effect Effects 0.000 claims description 3
• 230000009385 viral infection Effects 0.000 claims description 3
• WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 2
• 102100029438 Nitric oxide synthase, inducible Human genes 0.000 claims description 2
• 101710089543 Nitric oxide synthase, inducible Proteins 0.000 claims description 2
• YEESKJGWJFYOOK-IJHYULJSSA-N leukotriene D4 Chemical compound CCCCC\C=C/C\C=C/C=C/C=C/[C@H]([C@@H](O)CCCC(O)=O)SC[C@H](N)C(=O)NCC(O)=O YEESKJGWJFYOOK-IJHYULJSSA-N 0.000 claims description 2
• 229910052744 lithium Inorganic materials 0.000 claims description 2
• 239000003795 chemical substances by application Substances 0.000 claims 2
• 206010011906 Death Diseases 0.000 claims 1
• 201000004624 Dermatitis Diseases 0.000 claims 1
• 235000010469 Glycine max Nutrition 0.000 claims 1
• 244000068988 Glycine max Species 0.000 claims 1
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• 208000019693 Lung disease Diseases 0.000 claims 1
• 206010030113 Oedema Diseases 0.000 claims 1
• 230000000573 anti-seizure effect Effects 0.000 claims 1
• 238000003556 assay Methods 0.000 claims 1
• 210000003445 biliary tract Anatomy 0.000 claims 1
• 230000007613 environmental effect Effects 0.000 claims 1
• 230000035876 healing Effects 0.000 claims 1
• 230000036031 hyperthermia Effects 0.000 claims 1
• 230000000968 intestinal effect Effects 0.000 claims 1
• 238000004519 manufacturing process Methods 0.000 claims 1
• 239000011159 matrix material Substances 0.000 claims 1
• 238000009448 modified atmosphere packaging Methods 0.000 claims 1
• 235000019837 monoammonium phosphate Nutrition 0.000 claims 1
• 238000000554 physical therapy Methods 0.000 claims 1
• 230000002940 repellent Effects 0.000 claims 1
• 239000005871 repellent Substances 0.000 claims 1
• 239000004575 stone Substances 0.000 claims 1
• 230000000144 pharmacologic effect Effects 0.000 abstract description 7
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• 150000007522 mineralic acids Chemical class 0.000 abstract description 6
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• 102000003837 Epithelial Sodium Channels Human genes 0.000 abstract description 4
• 108090000140 Epithelial Sodium Channels Proteins 0.000 abstract description 4
• 230000002401 inhibitory effect Effects 0.000 abstract description 2
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 63
• 239000000543 intermediate Substances 0.000 description 63
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 54
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 52
• -1 EGFR-inhibitors Substances 0.000 description 48
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 45
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 44
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 37
• DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 35
• 239000000243 solution Substances 0.000 description 32
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 30
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 27
• GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 26
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 25
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
• 239000012071 phase Substances 0.000 description 24
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 23
• 230000002829 reductive effect Effects 0.000 description 22
• 229910052799 carbon Inorganic materials 0.000 description 21
• 239000011541 reaction mixture Substances 0.000 description 21
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 20
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 20
• 229940002612 prodrug Drugs 0.000 description 20
• 239000000651 prodrug Substances 0.000 description 20
• 125000003118 aryl group Chemical group 0.000 description 19
• 201000003883 Cystic fibrosis Diseases 0.000 description 18
• 125000005842 heteroatom Chemical group 0.000 description 18
• 239000012453 solvate Substances 0.000 description 18
• 150000004677 hydrates Chemical class 0.000 description 17
• 125000004432 carbon atom Chemical group C* 0.000 description 16
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
• 238000000119 electrospray ionisation mass spectrum Methods 0.000 description 15
• 238000003786 synthesis reaction Methods 0.000 description 15
• 239000003643 water by type Substances 0.000 description 15
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 14
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
• 239000013543 active substance Substances 0.000 description 14
• 150000003254 radicals Chemical class 0.000 description 13
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 12
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 12
• 238000004128 high performance liquid chromatography Methods 0.000 description 12
• XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 12
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 12
• 229920006395 saturated elastomer Polymers 0.000 description 12
• CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 11
• FIMXSEMBHGTNKT-UHFFFAOYSA-N Scopine Natural products CN1C2CC(O)CC1C1C2O1 FIMXSEMBHGTNKT-UHFFFAOYSA-N 0.000 description 11
• 239000007858 starting material Substances 0.000 description 11
• CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 10
• 150000007513 acids Chemical class 0.000 description 10
• 239000002585 base Substances 0.000 description 10
• 125000000623 heterocyclic group Chemical group 0.000 description 10
• 230000014759 maintenance of location Effects 0.000 description 10
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• 238000006243 chemical reaction Methods 0.000 description 9
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• 239000012043 crude product Substances 0.000 description 9
• 235000011167 hydrochloric acid Nutrition 0.000 description 9
• 229910052760 oxygen Inorganic materials 0.000 description 9
• 229910052717 sulfur Inorganic materials 0.000 description 9
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 8
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• 230000015572 biosynthetic process Effects 0.000 description 8
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• FIMXSEMBHGTNKT-RZVDLVGDSA-N scopine Chemical compound C([C@@H]1N2C)[C@H](O)C[C@@H]2[C@@H]2[C@H]1O2 FIMXSEMBHGTNKT-RZVDLVGDSA-N 0.000 description 8
• 125000001424 substituent group Chemical group 0.000 description 8
• XQJMXPAEFMWDOZ-UHFFFAOYSA-N 3exo-benzoyloxy-tropane Natural products CN1C(C2)CCC1CC2OC(=O)C1=CC=CC=C1 XQJMXPAEFMWDOZ-UHFFFAOYSA-N 0.000 description 7
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
• VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 7
• QQXLDOJGLXJCSE-UHFFFAOYSA-N N-methylnortropinone Natural products C1C(=O)CC2CCC1N2C QQXLDOJGLXJCSE-UHFFFAOYSA-N 0.000 description 7
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• 238000004007 reversed phase HPLC Methods 0.000 description 7
• VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 7
• 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 6
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• 125000002950 monocyclic group Chemical group 0.000 description 6
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• BPXUIMFOWKBCMM-UHFFFAOYSA-N 3,5-diamino-6-chloro-n-[n'-[[4-(2-phenylethyl)piperidin-4-yl]methyl]carbamimidoyl]pyrazine-2-carboxamide Chemical compound N1=C(Cl)C(N)=NC(N)=C1C(=O)NC(=N)NCC1(CCC=2C=CC=CC=2)CCNCC1 BPXUIMFOWKBCMM-UHFFFAOYSA-N 0.000 description 5
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• 125000000446 sulfanediyl group Chemical group *S* 0.000 description 5
• WXTMDXOMEHJXQO-UHFFFAOYSA-N 2,5-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC(O)=CC=C1O WXTMDXOMEHJXQO-UHFFFAOYSA-N 0.000 description 4
• VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
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• GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 4
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• 238000005804 alkylation reaction Methods 0.000 description 4
• XSDQTOBWRPYKKA-UHFFFAOYSA-N amiloride Chemical class NC(=N)NC(=O)C1=NC(Cl)=C(N)N=C1N XSDQTOBWRPYKKA-UHFFFAOYSA-N 0.000 description 4
• 239000003963 antioxidant agent Substances 0.000 description 4
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• 239000003246 corticosteroid Substances 0.000 description 4
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• 238000013461 design Methods 0.000 description 4
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• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
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• 125000001072 heteroaryl group Chemical group 0.000 description 4
• 238000005984 hydrogenation reaction Methods 0.000 description 4
• INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 4
• 229960001375 lactose Drugs 0.000 description 4
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• OKNSUWJNTAEWEN-UHFFFAOYSA-N methyl n'-(3,5-diamino-6-chloropyrazine-2-carbonyl)carbamimidothioate Chemical compound CSC(=N)NC(=O)C1=NC(Cl)=C(N)N=C1N OKNSUWJNTAEWEN-UHFFFAOYSA-N 0.000 description 4
• 239000002829 mitogen activated protein kinase inhibitor Substances 0.000 description 4
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• 239000011593 sulfur Chemical group 0.000 description 4
• DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 4
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
• BRKULQOUSCHDGS-UHFFFAOYSA-N 1,2-bis(4-fluorophenyl)ethane-1,2-dione Chemical compound C1=CC(F)=CC=C1C(=O)C(=O)C1=CC=C(F)C=C1 BRKULQOUSCHDGS-UHFFFAOYSA-N 0.000 description 3
• HRYOZNIRSNUJKM-UHFFFAOYSA-N 2-[4-[[[amino-[(3,5-diamino-6-chloropyrazine-2-carbonyl)amino]methylidene]amino]methyl]-4-(2-phenylethyl)piperidin-1-yl]acetic acid Chemical compound C1CN(CC(O)=O)CCC1(CCC=1C=CC=CC=1)CN=C(N)NC(=O)C1=NC(Cl)=C(N)N=C1N HRYOZNIRSNUJKM-UHFFFAOYSA-N 0.000 description 3
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• NMGODFWGUBLTTA-UHFFFAOYSA-N 3-amino-1h-quinazoline-2,4-dione Chemical compound C1=CC=C2C(=O)N(N)C(=O)NC2=C1 NMGODFWGUBLTTA-UHFFFAOYSA-N 0.000 description 3
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• FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 3
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• FXXQDYPNDZFBMV-UHFFFAOYSA-N methyl 5-cyano-5-[3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl]-2-oxocyclohexane-1-carboxylate Chemical compound C1CC(=O)C(C(=O)OC)CC1(C#N)C1=CC=C(OC(F)F)C(OCC2CC2)=C1 FXXQDYPNDZFBMV-UHFFFAOYSA-N 0.000 description 1
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• RRIRDPSOCUCGBV-UHFFFAOYSA-N methylenedioxyphenethylamine Chemical compound NCCC1=CC=C2OCOC2=C1 RRIRDPSOCUCGBV-UHFFFAOYSA-N 0.000 description 1
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• 239000011707 mineral Substances 0.000 description 1
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