NZ237566A

NZ237566A - Substituted amide and hydroxyamine derivatives and pharmaceutical compositions

Substituted amide and hydroxyamine derivatives and pharmaceutical compositions

Info

Publication number: NZ237566A
Authority: NZ; New Zealand
Prior art keywords: alkyl; formula; hydrogen; value; hydroxyurea
Prior art date: 1990-03-27

Application number

NZ237566A

Other languages

English (en)

Inventor

Jerry Leroy Adams

Don Edgar Griswold

Stanley James Schmidt

Ravi Shanker Garigipati

Original Assignee

Smithkline Beecham Corp

Priority date

1990-03-27

Filing date

1991-03-25

Publication date

1994-03-25

1991-03-25 Application filed by Smithkline Beecham Corp filed Critical Smithkline Beecham Corp

1994-03-25 Publication of NZ237566A publication Critical patent/NZ237566A/en

Links

AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical class ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 title claims description 53
239000008194 pharmaceutical composition Chemical class 0.000 title claims description 11
150000001408 amides Chemical class 0.000 title 1
150000001875 compounds Chemical class 0.000 claims description 290
239000000243 solution Substances 0.000 claims description 149
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 113
239000002904 solvent Substances 0.000 claims description 111
-1 arylalkyl heteroaryl Chemical group 0.000 claims description 97
238000000034 method Methods 0.000 claims description 89
239000001257 hydrogen Substances 0.000 claims description 88
229910052739 hydrogen Inorganic materials 0.000 claims description 88
125000000217 alkyl group Chemical group 0.000 claims description 84
230000002829 reductive effect Effects 0.000 claims description 67
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 64
239000007787 solid Substances 0.000 claims description 62
102000001381 Arachidonate 5-Lipoxygenase Human genes 0.000 claims description 52
108010093579 Arachidonate 5-lipoxygenase Proteins 0.000 claims description 52
150000002431 hydrogen Chemical group 0.000 claims description 43
150000002923 oximes Chemical class 0.000 claims description 40
238000011282 treatment Methods 0.000 claims description 38
NIZHERJWXFHGGU-UHFFFAOYSA-N isocyanato(trimethyl)silane Chemical compound C[Si](C)(C)N=C=O NIZHERJWXFHGGU-UHFFFAOYSA-N 0.000 claims description 37
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 36
VSNHCAURESNICA-UHFFFAOYSA-N Hydroxyurea Chemical class NC(=O)NO VSNHCAURESNICA-UHFFFAOYSA-N 0.000 claims description 32
DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 claims description 32
150000003839 salts Chemical class 0.000 claims description 31
OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 claims description 30
150000001412 amines Chemical class 0.000 claims description 29
239000002585 base Substances 0.000 claims description 29
229910052717 sulfur Chemical group 0.000 claims description 29
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 28
125000003118 aryl group Chemical group 0.000 claims description 26
239000002253 acid Substances 0.000 claims description 25
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 24
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 24
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 22
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 22
229910052736 halogen Inorganic materials 0.000 claims description 22
150000002367 halogens Chemical group 0.000 claims description 22
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 21
201000010099 disease Diseases 0.000 claims description 21
230000008569 process Effects 0.000 claims description 21
150000002443 hydroxylamines Chemical class 0.000 claims description 20
125000003545 alkoxy group Chemical group 0.000 claims description 19
125000005843 halogen group Chemical group 0.000 claims description 19
229960001330 hydroxycarbamide Drugs 0.000 claims description 19
230000001404 mediated effect Effects 0.000 claims description 19
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 19
102000003820 Lipoxygenases Human genes 0.000 claims description 18
108090000128 Lipoxygenases Proteins 0.000 claims description 18
125000001072 heteroaryl group Chemical group 0.000 claims description 18
125000003435 aroyl group Chemical group 0.000 claims description 17
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 17
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 16
229940093495 ethanethiol Drugs 0.000 claims description 16
230000002401 inhibitory effect Effects 0.000 claims description 16
239000011734 sodium Substances 0.000 claims description 16
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 15
125000003342 alkenyl group Chemical group 0.000 claims description 15
239000003960 organic solvent Substances 0.000 claims description 15
229910052760 oxygen Inorganic materials 0.000 claims description 15
229910052708 sodium Inorganic materials 0.000 claims description 15
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 14
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 claims description 14
239000012346 acetyl chloride Substances 0.000 claims description 14
239000003929 acidic solution Substances 0.000 claims description 14
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 14
125000004093 cyano group Chemical group *C#N 0.000 claims description 14
239000001301 oxygen Substances 0.000 claims description 14
239000011593 sulfur Chemical group 0.000 claims description 14
230000002378 acidificating effect Effects 0.000 claims description 12
GKKCIDNWFBPDBW-UHFFFAOYSA-M potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 claims description 12
125000001424 substituent group Chemical group 0.000 claims description 12
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 11
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 11
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 11
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 11
NBLAIKHFQBOVPV-UHFFFAOYSA-N bis(ethoxycarbonyl)azaniumylideneazanide Chemical compound CCOC(=O)[N+](=[N-])C(=O)OCC NBLAIKHFQBOVPV-UHFFFAOYSA-N 0.000 claims description 11
125000001188 haloalkyl group Chemical group 0.000 claims description 11
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 11
XWKFPIODWVPXLX-UHFFFAOYSA-N 2-methyl-5-methylpyridine Natural products CC1=CC=C(C)N=C1 XWKFPIODWVPXLX-UHFFFAOYSA-N 0.000 claims description 10
CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical compound NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 claims description 10
KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims description 10
241000282414 Homo sapiens Species 0.000 claims description 10
230000000202 analgesic effect Effects 0.000 claims description 10
125000003710 aryl alkyl group Chemical group 0.000 claims description 10
125000002541 furyl group Chemical group 0.000 claims description 10
125000001624 naphthyl group Chemical group 0.000 claims description 10
229910052757 nitrogen Chemical group 0.000 claims description 10
125000000753 cycloalkyl group Chemical group 0.000 claims description 9
239000003937 drug carrier Substances 0.000 claims description 9
125000004076 pyridyl group Chemical group 0.000 claims description 9
125000001544 thienyl group Chemical group 0.000 claims description 9
241000124008 Mammalia Species 0.000 claims description 8
125000004104 aryloxy group Chemical group 0.000 claims description 8
239000003085 diluting agent Substances 0.000 claims description 8
125000005956 isoquinolyl group Chemical group 0.000 claims description 8
125000000842 isoxazolyl group Chemical group 0.000 claims description 8
125000002971 oxazolyl group Chemical group 0.000 claims description 8
125000005493 quinolyl group Chemical group 0.000 claims description 8
125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 8
125000000335 thiazolyl group Chemical group 0.000 claims description 8
125000001425 triazolyl group Chemical group 0.000 claims description 8
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 7
238000010306 acid treatment Methods 0.000 claims description 7
150000001768 cations Chemical class 0.000 claims description 7
238000005984 hydrogenation reaction Methods 0.000 claims description 7
230000007062 hydrolysis Effects 0.000 claims description 7
238000006460 hydrolysis reaction Methods 0.000 claims description 7
201000004681 Psoriasis Diseases 0.000 claims description 6
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 6
150000008044 alkali metal hydroxides Chemical class 0.000 claims description 6
125000005842 heteroatom Chemical group 0.000 claims description 6
238000010626 work up procedure Methods 0.000 claims description 6
NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical group C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 claims description 5
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 5
125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 5
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 5
125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 5
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
201000008482 osteoarthritis Diseases 0.000 claims description 5
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims description 5
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 4
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 4
208000022559 Inflammatory bowel disease Diseases 0.000 claims description 4
229910001854 alkali hydroxide Inorganic materials 0.000 claims description 4
206010003246 arthritis Diseases 0.000 claims description 4
UWTDFICHZKXYAC-UHFFFAOYSA-N boron;oxolane Chemical compound [B].C1CCOC1 UWTDFICHZKXYAC-UHFFFAOYSA-N 0.000 claims description 4
SJGALSBBFTYSBA-UHFFFAOYSA-N oxaziridine Chemical compound C1NO1 SJGALSBBFTYSBA-UHFFFAOYSA-N 0.000 claims description 4
230000001590 oxidative effect Effects 0.000 claims description 4
ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 claims description 4
206010039073 rheumatoid arthritis Diseases 0.000 claims description 4
125000000547 substituted alkyl group Chemical group 0.000 claims description 4
125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 4
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 3
201000001320 Atherosclerosis Diseases 0.000 claims description 3
201000004624 Dermatitis Diseases 0.000 claims description 3
201000005569 Gout Diseases 0.000 claims description 3
206010063837 Reperfusion injury Diseases 0.000 claims description 3
208000006011 Stroke Diseases 0.000 claims description 3
229910052783 alkali metal Inorganic materials 0.000 claims description 3
125000005002 aryl methyl group Chemical group 0.000 claims description 3
208000006673 asthma Diseases 0.000 claims description 3
150000001540 azides Chemical class 0.000 claims description 3
UORVGPXVDQYIDP-BJUDXGSMSA-N borane Chemical class [10BH3] UORVGPXVDQYIDP-BJUDXGSMSA-N 0.000 claims description 3
LRJRPHROCLHMHK-UHFFFAOYSA-N boron;n,n-dimethylmethanamine Chemical compound [B].CN(C)C LRJRPHROCLHMHK-UHFFFAOYSA-N 0.000 claims description 3
FFHWGQQFANVOHV-UHFFFAOYSA-N dimethyldioxirane Chemical compound CC1(C)OO1 FFHWGQQFANVOHV-UHFFFAOYSA-N 0.000 claims description 3
MKRTXPORKIRPDG-UHFFFAOYSA-N diphenylphosphoryl azide Chemical compound C=1C=CC=CC=1P(=O)(N=[N+]=[N-])C1=CC=CC=C1 MKRTXPORKIRPDG-UHFFFAOYSA-N 0.000 claims description 3
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 claims description 3
208000020431 spinal cord injury Diseases 0.000 claims description 3
UYTMLDBQFLIQJA-XQRVVYSFSA-N (nz)-n-(furan-2-ylmethylidene)hydroxylamine Chemical compound O\N=C/C1=CC=CO1 UYTMLDBQFLIQJA-XQRVVYSFSA-N 0.000 claims description 2
206010039085 Rhinitis allergic Diseases 0.000 claims description 2
229910000288 alkali metal carbonate Inorganic materials 0.000 claims description 2
150000008041 alkali metal carbonates Chemical class 0.000 claims description 2
201000010105 allergic rhinitis Diseases 0.000 claims description 2
229910052782 aluminium Inorganic materials 0.000 claims description 2
235000019270 ammonium chloride Nutrition 0.000 claims description 2
NJAPCAIWQRPQPY-UHFFFAOYSA-N benzyl hydrogen carbonate Chemical group OC(=O)OCC1=CC=CC=C1 NJAPCAIWQRPQPY-UHFFFAOYSA-N 0.000 claims description 2
NNTOJPXOCKCMKR-UHFFFAOYSA-N boron;pyridine Chemical compound [B].C1=CC=NC=C1 NNTOJPXOCKCMKR-UHFFFAOYSA-N 0.000 claims description 2
150000008280 chlorinated hydrocarbons Chemical class 0.000 claims description 2
OIKHZBFJHONJJB-UHFFFAOYSA-N dimethyl(phenyl)silicon Chemical compound C[Si](C)C1=CC=CC=C1 OIKHZBFJHONJJB-UHFFFAOYSA-N 0.000 claims description 2
230000000302 ischemic effect Effects 0.000 claims description 2
SQDFHQJTAWCFIB-UHFFFAOYSA-N n-methylidenehydroxylamine Chemical compound ON=C SQDFHQJTAWCFIB-UHFFFAOYSA-N 0.000 claims description 2
125000003107 substituted aryl group Chemical group 0.000 claims description 2
125000005490 tosylate group Chemical group 0.000 claims description 2
125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 claims description 2
125000004390 alkyl sulfonyl group Chemical group 0.000 claims 4
125000004414 alkyl thio group Chemical group 0.000 claims 4
208000030886 Traumatic Brain injury Diseases 0.000 claims 2
208000037891 myocardial injury Diseases 0.000 claims 2
230000009529 traumatic brain injury Effects 0.000 claims 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
QDKWLJJOYIFEBS-UHFFFAOYSA-N 1-fluoro-4-$l^{1}-oxidanylbenzene Chemical group [O]C1=CC=C(F)C=C1 QDKWLJJOYIFEBS-UHFFFAOYSA-N 0.000 claims 1
206010001052 Acute respiratory distress syndrome Diseases 0.000 claims 1
208000013616 Respiratory Distress Syndrome Diseases 0.000 claims 1
208000011341 adult acute respiratory distress syndrome Diseases 0.000 claims 1
201000000028 adult respiratory distress syndrome Diseases 0.000 claims 1
239000004411 aluminium Substances 0.000 claims 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims 1
238000003776 cleavage reaction Methods 0.000 claims 1
125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims 1
208000028867 ischemia Diseases 0.000 claims 1
230000007017 scission Effects 0.000 claims 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims 1
125000003944 tolyl group Chemical group 0.000 claims 1
239000000203 mixture Substances 0.000 description 185
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 124
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 104
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 102
229910001868 water Inorganic materials 0.000 description 102
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 98
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 87
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 80
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 73
229920006395 saturated elastomer Polymers 0.000 description 68
239000011780 sodium chloride Substances 0.000 description 62
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 61
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 52
235000019439 ethyl acetate Nutrition 0.000 description 50
238000005481 NMR spectroscopy Methods 0.000 description 47
230000037361 pathway Effects 0.000 description 45
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 44
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 42
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 39
239000000284 extract Substances 0.000 description 38
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 38
239000011541 reaction mixture Substances 0.000 description 36
238000003818 flash chromatography Methods 0.000 description 35
239000003112 inhibitor Substances 0.000 description 30
239000000543 intermediate Substances 0.000 description 29
YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 27
239000000047 product Substances 0.000 description 27
238000003756 stirring Methods 0.000 description 27
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 24
238000001914 filtration Methods 0.000 description 23
VNYSSYRCGWBHLG-AMOLWHMGSA-N leukotriene B4 Chemical compound CCCCC\C=C/C[C@@H](O)\C=C\C=C\C=C/[C@@H](O)CCCC(O)=O VNYSSYRCGWBHLG-AMOLWHMGSA-N 0.000 description 23
238000000262 chemical ionisation mass spectrometry Methods 0.000 description 21
238000006243 chemical reaction Methods 0.000 description 21
230000000694 effects Effects 0.000 description 21
229910000069 nitrogen hydride Inorganic materials 0.000 description 21
238000000746 purification Methods 0.000 description 21
241001465754 Metazoa Species 0.000 description 20
230000005764 inhibitory process Effects 0.000 description 20
239000000725 suspension Substances 0.000 description 20
229910052943 magnesium sulfate Inorganic materials 0.000 description 19
239000012300 argon atmosphere Substances 0.000 description 18
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 17
229910000104 sodium hydride Inorganic materials 0.000 description 17
OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 16
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
238000002360 preparation method Methods 0.000 description 16
238000010992 reflux Methods 0.000 description 16
UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 15
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 14
238000004519 manufacturing process Methods 0.000 description 14
239000012312 sodium hydride Substances 0.000 description 14
235000011121 sodium hydroxide Nutrition 0.000 description 14
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 13
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 13
239000002480 mineral oil Substances 0.000 description 13
235000010446 mineral oil Nutrition 0.000 description 13
229910000029 sodium carbonate Inorganic materials 0.000 description 13
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 12
239000004480 active ingredient Substances 0.000 description 12
229940114079 arachidonic acid Drugs 0.000 description 12
235000021342 arachidonic acid Nutrition 0.000 description 12
210000004369 blood Anatomy 0.000 description 12
239000008280 blood Substances 0.000 description 12
229910000085 borane Inorganic materials 0.000 description 12
206010061218 Inflammation Diseases 0.000 description 11
230000004054 inflammatory process Effects 0.000 description 11
210000004027 cell Anatomy 0.000 description 10
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
239000007858 starting material Substances 0.000 description 9
FNSQPQKPPGALFA-UHFFFAOYSA-N 6-hydroxy-3,4-dihydro-2h-naphthalen-1-one Chemical compound O=C1CCCC2=CC(O)=CC=C21 FNSQPQKPPGALFA-UHFFFAOYSA-N 0.000 description 8
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
239000003795 chemical substances by application Substances 0.000 description 8
238000004587 chromatography analysis Methods 0.000 description 8
238000009472 formulation Methods 0.000 description 8
210000001616 monocyte Anatomy 0.000 description 8
KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
229910000027 potassium carbonate Inorganic materials 0.000 description 8
230000009467 reduction Effects 0.000 description 8
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