DE69635231T2 - Selektive Inhibitoren viraler oder bakterieller Neuraminidase - Google Patents

Info

Publication number

DE69635231T2

DE69635231T2 DE69635231T DE69635231T DE69635231T2 DE 69635231 T2 DE69635231 T2 DE 69635231T2 DE 69635231 T DE69635231 T DE 69635231T DE 69635231 T DE69635231 T DE 69635231T DE 69635231 T2 DE69635231 T2 DE 69635231T2

Authority

DE

Germany

Prior art keywords

compound

mmol

nitro

solution

acid

Prior art date

1995-02-27

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.)

Expired - Lifetime

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• 108010006232 Neuraminidase Proteins 0.000 title claims abstract description 37
• 102000005348 Neuraminidase Human genes 0.000 title claims abstract description 36
• 230000001580 bacterial effect Effects 0.000 title description 3
• 230000003612 virological effect Effects 0.000 title description 3
• 229940124639 Selective inhibitor Drugs 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 419
• 238000000034 method Methods 0.000 claims abstract description 225
• -1 antibodies Substances 0.000 claims abstract description 84
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 20
• 230000000694 effects Effects 0.000 claims abstract description 12
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 8
• 230000002401 inhibitory effect Effects 0.000 claims abstract description 6
• 238000002360 preparation method Methods 0.000 claims description 37
• 238000011282 treatment Methods 0.000 claims description 24
• 150000003839 salts Chemical class 0.000 claims description 19
• 125000000217 alkyl group Chemical group 0.000 claims description 7
• 206010022000 influenza Diseases 0.000 claims description 6
• 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 claims description 5
• 238000011321 prophylaxis Methods 0.000 claims description 5
• 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims description 3
• 239000003937 drug carrier Substances 0.000 claims description 2
• 239000012453 solvate Substances 0.000 claims description 2
• 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
• 230000002378 acidificating effect Effects 0.000 abstract description 50
• 229920000642 polymer Polymers 0.000 abstract description 13
• 239000003112 inhibitor Substances 0.000 abstract description 4
• 238000003556 assay Methods 0.000 abstract description 2
• 239000000463 material Substances 0.000 abstract description 2
• 150000001335 aliphatic alkanes Chemical class 0.000 abstract 1
• 230000000890 antigenic effect Effects 0.000 abstract 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 327
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 225
• 239000000243 solution Substances 0.000 description 160
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 138
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 128
• 235000019439 ethyl acetate Nutrition 0.000 description 125
• 238000006243 chemical reaction Methods 0.000 description 124
• 239000000203 mixture Substances 0.000 description 124
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 120
• 238000005160 1H NMR spectroscopy Methods 0.000 description 102
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 99
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 97
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 87
• 239000007787 solid Substances 0.000 description 76
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 71
• 235000019441 ethanol Nutrition 0.000 description 70
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 68
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 64
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 60
• 238000003818 flash chromatography Methods 0.000 description 55
• 239000002904 solvent Substances 0.000 description 54
• 150000001412 amines Chemical class 0.000 description 52
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• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 50
• 239000012267 brine Substances 0.000 description 49
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• 229920005989 resin Polymers 0.000 description 43
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• NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 42
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 42
• 239000003153 chemical reaction reagent Substances 0.000 description 41
• 150000001540 azides Chemical class 0.000 description 40
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• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 36
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• 230000003213 activating effect Effects 0.000 description 33
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• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 32
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 30
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
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• PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 26
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• DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 26
• VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 25
• 239000003480 eluent Substances 0.000 description 25
• QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 25
• 238000003786 synthesis reaction Methods 0.000 description 25
• 239000000126 substance Substances 0.000 description 24
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 23
• 238000003756 stirring Methods 0.000 description 23
• 150000002009 diols Chemical class 0.000 description 22
• 150000002148 esters Chemical class 0.000 description 22
• 125000006239 protecting group Chemical group 0.000 description 22
• RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 22
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 21
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 20
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 20
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 20
• 239000012044 organic layer Substances 0.000 description 20
• 230000002829 reductive effect Effects 0.000 description 20
• 229920001429 chelating resin Polymers 0.000 description 19
• 238000006467 substitution reaction Methods 0.000 description 18
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 18
• 239000012043 crude product Substances 0.000 description 17
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 16
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 16
• 239000012074 organic phase Substances 0.000 description 16
• 150000002924 oxiranes Chemical class 0.000 description 16
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
• 230000004913 activation Effects 0.000 description 15
• 238000001994 activation Methods 0.000 description 15
• 239000003638 chemical reducing agent Substances 0.000 description 15
• 150000004702 methyl esters Chemical class 0.000 description 15
• 230000009467 reduction Effects 0.000 description 15
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 14
• 239000012359 Methanesulfonyl chloride Substances 0.000 description 14
• 239000000284 extract Substances 0.000 description 14
• 230000002163 immunogen Effects 0.000 description 14
• 230000009466 transformation Effects 0.000 description 14
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 13
• 239000006260 foam Substances 0.000 description 13
• 239000007788 liquid Substances 0.000 description 13
• GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 12
• 229960000549 4-dimethylaminophenol Drugs 0.000 description 12
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-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
• 238000004519 manufacturing process Methods 0.000 description 12
• VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 12
• 239000012038 nucleophile Substances 0.000 description 12
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• JXOHGGNKMLTUBP-HSUXUTPPSA-N shikimic acid Chemical compound O[C@@H]1CC(C(O)=O)=C[C@@H](O)[C@H]1O JXOHGGNKMLTUBP-HSUXUTPPSA-N 0.000 description 12
• JXOHGGNKMLTUBP-JKUQZMGJSA-N shikimic acid Natural products O[C@@H]1CC(C(O)=O)=C[C@H](O)[C@@H]1O JXOHGGNKMLTUBP-JKUQZMGJSA-N 0.000 description 12
• WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 11
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• SKMKJBYBPYBDMN-RYUDHWBXSA-N 3-(difluoromethoxy)-5-[2-(3,3-difluoropyrrolidin-1-yl)-6-[(1s,4s)-2-oxa-5-azabicyclo[2.2.1]heptan-5-yl]pyrimidin-4-yl]pyridin-2-amine Chemical compound C1=C(OC(F)F)C(N)=NC=C1C1=CC(N2[C@H]3C[C@H](OC3)C2)=NC(N2CC(F)(F)CC2)=N1 SKMKJBYBPYBDMN-RYUDHWBXSA-N 0.000 description 10
• YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 10
• ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 10
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