SK136799A3 - Compounds and compositions for treating diseases associated with serine protease, particularly tryptase, activity - Google Patents

Compounds and compositions for treating diseases associated with serine protease, particularly tryptase, activity Download PDF

Info

Publication number: SK136799A3
Authority: SK; Slovakia
Prior art keywords: alkyl; benzoimidazol; ethyl; compound; methyl
Prior art date: 1997-04-07

Application number

SK1367-99A

Other languages

English (en)

Slovak (sk)

Inventor

Timothy J Church

Neil Scott Cutshall

Anthony R Gangloff

Thomas E Jenkins

Martin S Linsell

Joane Litvak

Kenneth D Rice

Jeffrey R Spencer

Vivian R Wang

Original Assignee

Axys Pharm Corp

Priority date (The priority date 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 date listed.)

1997-04-07

Filing date

1997-12-01

Publication date

2000-07-11

1997-12-01 Application filed by Axys Pharm Corp filed Critical Axys Pharm Corp

2000-07-11 Publication of SK136799A3 publication Critical patent/SK136799A3/sk

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 372
239000000203 mixture Substances 0.000 title claims abstract description 140
108060005989 Tryptase Proteins 0.000 title abstract description 24
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title description 26
201000010099 disease Diseases 0.000 title description 24
102000001400 Tryptase Human genes 0.000 title description 23
230000000694 effects Effects 0.000 title description 12
102000012479 Serine Proteases Human genes 0.000 title description 4
108010022999 Serine Proteases Proteins 0.000 title description 4
125000000217 alkyl group Chemical group 0.000 claims abstract description 122
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 63
239000001257 hydrogen Substances 0.000 claims abstract description 62
238000000034 method Methods 0.000 claims abstract description 53
125000003545 alkoxy group Chemical group 0.000 claims abstract description 46
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 46
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 43
125000001424 substituent group Chemical group 0.000 claims abstract description 38
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 19
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 18
125000003943 azolyl group Chemical group 0.000 claims abstract description 14
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims abstract description 11
150000002431 hydrogen Chemical class 0.000 claims abstract description 10
238000002360 preparation method Methods 0.000 claims abstract description 10
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 9
206010010741 Conjunctivitis Diseases 0.000 claims abstract description 6
206010039073 rheumatoid arthritis Diseases 0.000 claims abstract description 6
210000002345 respiratory system Anatomy 0.000 claims abstract description 5
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract 5
-1 amino, carboxy, carbamoyl Chemical group 0.000 claims description 317
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 132
125000005842 heteroatom Chemical group 0.000 claims description 73
125000003118 aryl group Chemical group 0.000 claims description 66
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 61
125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 50
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 48
125000002947 alkylene group Chemical group 0.000 claims description 37
150000003839 salts Chemical class 0.000 claims description 34
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 28
229910052736 halogen Inorganic materials 0.000 claims description 26
150000002367 halogens Chemical class 0.000 claims description 26
239000000651 prodrug Substances 0.000 claims description 26
229940002612 prodrug Drugs 0.000 claims description 26
150000001204 N-oxides Chemical class 0.000 claims description 24
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 22
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 22
230000004054 inflammatory process Effects 0.000 claims description 22
125000006514 pyridin-2-ylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 22
125000006413 ring segment Chemical group 0.000 claims description 22
206010061218 Inflammation Diseases 0.000 claims description 21
125000001931 aliphatic group Chemical group 0.000 claims description 21
125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 20
239000005711 Benzoic acid Substances 0.000 claims description 20
235000010233 benzoic acid Nutrition 0.000 claims description 20
125000004432 carbon atom Chemical group C* 0.000 claims description 20
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 18
125000002723 alicyclic group Chemical group 0.000 claims description 17
FNLQDVXHDNFXIY-UHFFFAOYSA-N 3h-benzimidazole-5-carboxamide Chemical compound NC(=O)C1=CC=C2NC=NC2=C1 FNLQDVXHDNFXIY-UHFFFAOYSA-N 0.000 claims description 16
125000004423 acyloxy group Chemical group 0.000 claims description 16
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims description 16
125000004429 atom Chemical group 0.000 claims description 14
125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 13
229930194542 Keto Natural products 0.000 claims description 12
241000124008 Mammalia Species 0.000 claims description 12
125000006239 protecting group Chemical group 0.000 claims description 12
239000000443 aerosol Substances 0.000 claims description 11
125000004414 alkyl thio group Chemical group 0.000 claims description 10
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 10
125000004093 cyano group Chemical group *C#N 0.000 claims description 10
125000003037 imidazol-2-yl group Chemical group [H]N1C([*])=NC([H])=C1[H] 0.000 claims description 10
239000008194 pharmaceutical composition Substances 0.000 claims description 10
125000000468 ketone group Chemical group 0.000 claims description 9
125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 claims description 9
125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 8
FEPAORUNILXIKL-UHFFFAOYSA-N C(CC)C=1NC2=C(N1)C=CC(=C2)C(=O)NCCC2=CC=CC1=CC=CC=C21 Chemical compound C(CC)C=1NC2=C(N1)C=CC(=C2)C(=O)NCCC2=CC=CC1=CC=CC=C21 FEPAORUNILXIKL-UHFFFAOYSA-N 0.000 claims description 8
239000003937 drug carrier Substances 0.000 claims description 8
125000002950 monocyclic group Chemical group 0.000 claims description 8
125000004287 oxazol-2-yl group Chemical group [H]C1=C([H])N=C(*)O1 0.000 claims description 8
230000008569 process Effects 0.000 claims description 8
125000005323 thioketone group Chemical group 0.000 claims description 8
125000003282 alkyl amino group Chemical group 0.000 claims description 7
125000005210 alkyl ammonium group Chemical group 0.000 claims description 7
125000005843 halogen group Chemical group 0.000 claims description 7
230000009385 viral infection Effects 0.000 claims description 7
MTWFINXLTMNGCU-UHFFFAOYSA-N 2-[2-[[3-methyl-2-[1-(4,6,7-trifluoro-1h-benzimidazol-2-yl)ethyl]benzimidazole-5-carbonyl]amino]ethoxy]benzoic acid Chemical compound N=1C2=C(F)C=C(F)C(F)=C2NC=1C(C)C(N(C1=C2)C)=NC1=CC=C2C(=O)NCCOC1=CC=CC=C1C(O)=O MTWFINXLTMNGCU-UHFFFAOYSA-N 0.000 claims description 6
208000036142 Viral infection Diseases 0.000 claims description 6
125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 6
229910052799 carbon Inorganic materials 0.000 claims description 6
125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims description 6
125000001118 alkylidene group Chemical group 0.000 claims description 5
125000004391 aryl sulfonyl group Chemical group 0.000 claims description 5
125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 5
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
238000010511 deprotection reaction Methods 0.000 claims description 5
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
125000004585 polycyclic heterocycle group Chemical group 0.000 claims description 5
125000004104 aryloxy group Chemical group 0.000 claims description 4
125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 4
229940125904 compound 1 Drugs 0.000 claims description 4
229940125782 compound 2 Drugs 0.000 claims description 4
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
125000002883 imidazolyl group Chemical group 0.000 claims description 4
239000000843 powder Substances 0.000 claims description 4
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 4
125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims description 3
FTNBVAOKBGAXCR-UHFFFAOYSA-N 2-[2-[[2-[1-(5-ethanimidoyl-3,4,6,7-tetrahydroimidazo[4,5-c]pyridin-2-yl)ethyl]-3-(2-methoxyethyl)benzimidazole-5-carbonyl]amino]ethoxy]benzoic acid Chemical compound C1=C2N(CCOC)C(C(C)C=3NC=4CCN(CC=4N=3)C(C)=N)=NC2=CC=C1C(=O)NCCOC1=CC=CC=C1C(O)=O FTNBVAOKBGAXCR-UHFFFAOYSA-N 0.000 claims description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
239000000808 adrenergic beta-agonist Substances 0.000 claims description 3
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 3
125000002619 bicyclic group Chemical group 0.000 claims description 3
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 3
FJUZLZZFUIJKRF-UHFFFAOYSA-N n-[2-(2-carbamoyl-4-chlorophenoxy)ethyl]-2-[1-[6-(diaminomethylideneamino)-1h-benzimidazol-2-yl]ethyl]-3-methylbenzimidazole-5-carboxamide Chemical compound N=1C2=CC(NC(N)=N)=CC=C2NC=1C(C)C(N(C1=C2)C)=NC1=CC=C2C(=O)NCCOC1=CC=C(Cl)C=C1C(N)=O FJUZLZZFUIJKRF-UHFFFAOYSA-N 0.000 claims description 3
WURDECGZGWCLLG-UHFFFAOYSA-N n-[2-(2-carbamoylphenoxy)ethyl]-2-[1-[6-(diaminomethylideneamino)-1h-benzimidazol-2-yl]ethyl]-3-methylbenzimidazole-5-carboxamide Chemical compound N=1C2=CC(NC(N)=N)=CC=C2NC=1C(C)C(N(C1=C2)C)=NC1=CC=C2C(=O)NCCOC1=CC=CC=C1C(N)=O WURDECGZGWCLLG-UHFFFAOYSA-N 0.000 claims description 3
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
125000003831 tetrazolyl group Chemical group 0.000 claims description 3
XWTYSIMOBUGWOL-UHFFFAOYSA-N (+-)-Terbutaline Chemical compound CC(C)(C)NCC(O)C1=CC(O)=CC(O)=C1 XWTYSIMOBUGWOL-UHFFFAOYSA-N 0.000 claims description 2
SYWNNHDBRIRLIJ-UHFFFAOYSA-N 2-[2-[[2-[1-(5-ethanimidoyl-3,4,6,7-tetrahydroimidazo[4,5-c]pyridin-2-yl)ethyl]-3-methylbenzimidazole-5-carbonyl]amino]ethoxy]benzoic acid Chemical compound N=1C=2CN(C(C)=N)CCC=2NC=1C(C)C(N(C1=C2)C)=NC1=CC=C2C(=O)NCCOC1=CC=CC=C1C(O)=O SYWNNHDBRIRLIJ-UHFFFAOYSA-N 0.000 claims description 2
JAHYJFMHHBGDKR-UHFFFAOYSA-N 2-[[6-(aminomethyl)-1h-benzimidazol-2-yl]methyl]-3-methyl-n-(2-naphthalen-1-ylethyl)benzimidazole-5-carboxamide Chemical compound C1=CC=C2C(CCNC(=O)C3=CC=C4N=C(CC=5NC6=CC=C(CN)C=C6N=5)N(C4=C3)C)=CC=CC2=C1 JAHYJFMHHBGDKR-UHFFFAOYSA-N 0.000 claims description 2
HAKZKUZTXPGYRU-UHFFFAOYSA-N 2-[[6-(aminomethyl)-4,5,6,7-tetrahydro-1h-benzimidazol-2-yl]methyl]-3-methyl-n-(2-naphthalen-1-ylethyl)benzimidazole-5-carboxamide Chemical compound C1=CC=C2C(CCNC(=O)C3=CC=C4N=C(CC=5NC=6CCC(CN)CC=6N=5)N(C4=C3)C)=CC=CC2=C1 HAKZKUZTXPGYRU-UHFFFAOYSA-N 0.000 claims description 2
PCCUPAKWDDHPKB-UHFFFAOYSA-N 5-chloro-2-[2-[[2-[1-[6-(diaminomethylideneamino)-1h-benzimidazol-2-yl]ethyl]-3-methylbenzimidazole-5-carbonyl]amino]ethoxy]benzoic acid Chemical compound N=1C2=CC(NC(N)=N)=CC=C2NC=1C(C)C(N(C1=C2)C)=NC1=CC=C2C(=O)NCCOC1=CC=C(Cl)C=C1C(O)=O PCCUPAKWDDHPKB-UHFFFAOYSA-N 0.000 claims description 2
OLZJYKTXRMALAB-UHFFFAOYSA-N C(C)C=1NC2=C(N1)C=CC(=C2)C(=O)NCCC2=CC=CC1=CC=CC=C21 Chemical compound C(C)C=1NC2=C(N1)C=CC(=C2)C(=O)NCCC2=CC=CC1=CC=CC=C21 OLZJYKTXRMALAB-UHFFFAOYSA-N 0.000 claims description 2
NDAUXUAQIAJITI-UHFFFAOYSA-N albuterol Chemical compound CC(C)(C)NCC(O)C1=CC=C(O)C(CO)=C1 NDAUXUAQIAJITI-UHFFFAOYSA-N 0.000 claims description 2
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 2
125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 2
229940126214 compound 3 Drugs 0.000 claims description 2
229960001022 fenoterol Drugs 0.000 claims description 2
LSLYOANBFKQKPT-UHFFFAOYSA-N fenoterol Chemical compound C=1C(O)=CC(O)=CC=1C(O)CNC(C)CC1=CC=C(O)C=C1 LSLYOANBFKQKPT-UHFFFAOYSA-N 0.000 claims description 2
229960002848 formoterol Drugs 0.000 claims description 2
BPZSYCZIITTYBL-UHFFFAOYSA-N formoterol Chemical compound C1=CC(OC)=CC=C1CC(C)NCC(O)C1=CC=C(O)C(NC=O)=C1 BPZSYCZIITTYBL-UHFFFAOYSA-N 0.000 claims description 2
239000002674 ointment Substances 0.000 claims description 2
229960002052 salbutamol Drugs 0.000 claims description 2
229960000195 terbutaline Drugs 0.000 claims description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
XMGODZOTGXEKCX-UHFFFAOYSA-N 2-(5-ethanimidoyl-3,4,6,7-tetrahydroimidazo[4,5-c]pyridine-2-carbonyl)-3-methyl-n-(2-naphthalen-1-ylethyl)benzimidazole-5-carboxamide Chemical compound C1=CC=C2C(CCNC(=O)C3=CC=C4N=C(N(C4=C3)C)C(=O)C=3NC=4CCN(CC=4N=3)C(=N)C)=CC=CC2=C1 XMGODZOTGXEKCX-UHFFFAOYSA-N 0.000 claims 1
239000003118 drug derivative Substances 0.000 claims 1
208000006673 asthma Diseases 0.000 abstract description 25
238000011282 treatment Methods 0.000 abstract description 23
210000003630 histaminocyte Anatomy 0.000 abstract description 12
208000027866 inflammatory disease Diseases 0.000 abstract description 8
206010039085 Rhinitis allergic Diseases 0.000 abstract description 5
201000010105 allergic rhinitis Diseases 0.000 abstract description 5
230000002265 prevention Effects 0.000 abstract description 5
229940124639 Selective inhibitor Drugs 0.000 abstract description 2
230000003389 potentiating effect Effects 0.000 abstract description 2
230000003612 virological effect Effects 0.000 abstract description 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 2
125000001475 halogen functional group Chemical group 0.000 abstract 2
208000022559 Inflammatory bowel disease Diseases 0.000 abstract 1
230000001404 mediated effect Effects 0.000 abstract 1
230000000699 topical effect Effects 0.000 abstract 1
238000001819 mass spectrum Methods 0.000 description 205
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 113
238000005160 1H NMR spectroscopy Methods 0.000 description 95
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 80
239000000243 solution Substances 0.000 description 65
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 60
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 55
239000007787 solid Substances 0.000 description 35
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 31
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 30
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 30
229940087827 biolon Drugs 0.000 description 30
239000002244 precipitate Substances 0.000 description 30
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 28
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
229920006395 saturated elastomer Polymers 0.000 description 26
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 22
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 20
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 20
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 20
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 16
239000012299 nitrogen atmosphere Substances 0.000 description 15
239000011780 sodium chloride Substances 0.000 description 15
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 14
229910000041 hydrogen chloride Inorganic materials 0.000 description 14
239000012071 phase Substances 0.000 description 13
241001494479 Pecora Species 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
238000001914 filtration Methods 0.000 description 12
229910052757 nitrogen Inorganic materials 0.000 description 12
239000012044 organic layer Substances 0.000 description 12
230000002829 reductive effect Effects 0.000 description 12
239000002253 acid Substances 0.000 description 11
238000006243 chemical reaction Methods 0.000 description 11
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
125000000753 cycloalkyl group Chemical group 0.000 description 10
230000004044 response Effects 0.000 description 10
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 9
239000003921 oil Substances 0.000 description 9
229910000030 sodium bicarbonate Inorganic materials 0.000 description 9
235000017557 sodium bicarbonate Nutrition 0.000 description 9
238000005481 NMR spectroscopy Methods 0.000 description 8
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 8
239000013566 allergen Substances 0.000 description 8
239000011734 sodium Substances 0.000 description 8
239000000126 substance Substances 0.000 description 8
210000001519 tissue Anatomy 0.000 description 8
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 7
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 7
239000000427 antigen Substances 0.000 description 7
102000036639 antigens Human genes 0.000 description 7
108091007433 antigens Proteins 0.000 description 7
239000002585 base Substances 0.000 description 7
239000010410 layer Substances 0.000 description 7
238000004895 liquid chromatography mass spectrometry Methods 0.000 description 7
230000002441 reversible effect Effects 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 6
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 6
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
241001465754 Metazoa Species 0.000 description 6
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 6
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
229960000583 acetic acid Drugs 0.000 description 6
238000002953 preparative HPLC Methods 0.000 description 6
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 6
BOEBOCVQDLZVBD-UHFFFAOYSA-N C1=CC=C2C(CCC3=NC4=CC=C(C=C4N3)C(=O)N)=CC=CC2=C1 Chemical compound C1=CC=C2C(CCC3=NC4=CC=C(C=C4N3)C(=O)N)=CC=CC2=C1 BOEBOCVQDLZVBD-UHFFFAOYSA-N 0.000 description 5
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KSAVQLQVUXSOCR-UHFFFAOYSA-M sodium lauroyl sarcosinate Chemical compound [Na+].CCCCCCCCCCCC(=O)N(C)CC([O-])=O KSAVQLQVUXSOCR-UHFFFAOYSA-M 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic 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
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/20—Two benzimidazolyl-2 radicals linked together directly or via a hydrocarbon or substituted hydrocarbon radical
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- 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
- C07D401/14—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 three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
General Chemical & Material Sciences (AREA)
Animal Behavior & Ethology (AREA)
Veterinary Medicine (AREA)
Pulmonology (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Pain & Pain Management (AREA)
Virology (AREA)
Communicable Diseases (AREA)
Oncology (AREA)
Immunology (AREA)
Rheumatology (AREA)
Otolaryngology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

SK1367-99A 1997-04-07 1997-12-01 Compounds and compositions for treating diseases associated with serine protease, particularly tryptase, activity SK136799A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US83367497A	1997-04-07	1997-04-07
PCT/US1997/021849 WO1998045275A1 (en)	1997-04-07	1997-12-01	Compounds and compositions for treating diseases associated with serine protease, particularly tryptase, activity

Publications (1)

Publication Number	Publication Date
SK136799A3 true SK136799A3 (en)	2000-07-11

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ID=25264996

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Application Number	Title	Priority Date	Filing Date
SK1367-99A SK136799A3 (en)	1997-04-07	1997-12-01	Compounds and compositions for treating diseases associated with serine protease, particularly tryptase, activity

Country Status (16)

Country	Link
EP (1)	EP1019382A1 (lt)
JP (1)	JP2001519806A (lt)
KR (1)	KR20010006119A (lt)
CN (1)	CN1251579A (lt)
AU (1)	AU752064B2 (lt)
CA (1)	CA2285454A1 (lt)
EE (1)	EE04055B1 (lt)
HU (1)	HUP0001522A3 (lt)
LT (1)	LT4704B (lt)
LV (1)	LV12495B (lt)
NO (1)	NO314183B1 (lt)
NZ (1)	NZ500029A (lt)
PL (1)	PL336233A1 (lt)
SI (1)	SI20115A (lt)
SK (1)	SK136799A3 (lt)
WO (1)	WO1998045275A1 (lt)

Families Citing this family (18)

* Cited by examiner, † Cited by third party
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US6221914B1 (en)	1997-11-10	2001-04-24	Array Biopharma Inc.	Sulfonamide bridging compounds that inhibit tryptase activity
WO1999026932A1 (en) *	1997-11-26	1999-06-03	Axys Pharmaceuticals, Inc.	By amidino group substituted heterocyclic derivatives and their use as anticoagulants
WO1999026933A1 (en) *	1997-11-26	1999-06-03	Axys Pharmaceuticals, Inc.	Substituted amidinoaryl derivatives and their use as anticoagulants
GT199900167A (es) *	1998-10-01	2001-03-21		Nuevos bis-benzimidazoles.
WO2000020400A1 (en) *	1998-10-05	2000-04-13	Axys Pharmaceuticals, Inc.	Novel compounds and compositions for treating hepatitis c infections
US6541486B1 (en) *	1999-06-04	2003-04-01	Elan Pharma International Ltd.	Bis-benzimidazole compounds and analogs thereof for inhibiting cell death
DE19953899A1 (de) *	1999-11-10	2001-05-17	Boehringer Ingelheim Pharma	Carboxamid-substituierte Benzimidazolderivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel
WO2001052883A1 (en) *	2000-01-20	2001-07-26	Amgen Inc.	Inhibitors of protease-activated receptor-2 (par-2) as novel asthma therapeutics
US6448281B1 (en) *	2000-07-06	2002-09-10	Boehringer Ingelheim (Canada) Ltd.	Viral polymerase inhibitors
DE10048715A1 (de) *	2000-09-30	2004-05-19	Grünenthal GmbH	Verwendung von Aminosäure zur Behandlung von Schmerz
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1997
- 1997-12-01 JP JP54273998A patent/JP2001519806A/ja active Pending
- 1997-12-01 KR KR1019997009197A patent/KR20010006119A/ko not_active Ceased
- 1997-12-01 HU HU0001522A patent/HUP0001522A3/hu unknown
- 1997-12-01 NZ NZ500029A patent/NZ500029A/en unknown
- 1997-12-01 AU AU58950/98A patent/AU752064B2/en not_active Ceased
- 1997-12-01 SK SK1367-99A patent/SK136799A3/sk unknown
- 1997-12-01 PL PL97336233A patent/PL336233A1/xx unknown
- 1997-12-01 CN CN97182098A patent/CN1251579A/zh active Pending
- 1997-12-01 EP EP97954520A patent/EP1019382A1/en not_active Withdrawn
- 1997-12-01 WO PCT/US1997/021849 patent/WO1998045275A1/en not_active Ceased
- 1997-12-01 CA CA002285454A patent/CA2285454A1/en not_active Abandoned
- 1997-12-01 EE EEP199900477A patent/EE04055B1/xx not_active IP Right Cessation
- 1997-12-01 SI SI9720094A patent/SI20115A/sl unknown
1999
- 1999-10-06 NO NO19994858A patent/NO314183B1/no unknown
- 1999-11-02 LV LVP-99-153A patent/LV12495B/en unknown
- 1999-11-05 LT LT99-131A patent/LT4704B/lt not_active IP Right Cessation

Also Published As

Publication number	Publication date
LV12495B (en)	2001-01-20
EP1019382A1 (en)	2000-07-19
AU5895098A (en)	1998-10-30
NO314183B1 (no)	2003-02-10
SI20115A (sl)	2000-06-30
AU752064B2 (en)	2002-09-05
LT4704B (lt)	2000-09-25
PL336233A1 (en)	2000-06-19
NO994858D0 (no)	1999-10-06
EE9900477A (et)	2000-06-15
NO994858L (no)	1999-12-06
KR20010006119A (ko)	2001-01-26
HUP0001522A2 (hu)	2001-05-28
CA2285454A1 (en)	1998-10-15
NZ500029A (en)	2001-02-23
CN1251579A (zh)	2000-04-26
EE04055B1 (et)	2003-06-16
LT99131A (lt)	2000-04-25
WO1998045275A1 (en)	1998-10-15
HUP0001522A3 (en)	2001-08-28
LV12495A (en)	2000-06-20
JP2001519806A (ja)	2001-10-23

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JP3120075B2 (ja)	2000-12-25	化合物
SK136799A3 (en)	2000-07-11	Compounds and compositions for treating diseases associated with serine protease, particularly tryptase, activity
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JPWO1997000258A1 (ja)	1998-08-25	三環性ベンゾアゼピン化合物
JPH10291988A (ja)	1998-11-04	複素環式化合物
CZ345499A3 (cs)	2000-07-12	Sloučeniny a prostředky pro léčbu nemocí spojených s aktivitou serinové proteasy, zejména tryptasy
MXPA99009006A (en)	2000-08-01	Compounds and compositions for treating diseases associated with serine protease, particularly tryptase, activity
HU221198B1 (en)	2002-08-28	Substituted imidazo[1,2-a]pyridinyl- or imidazolyl-cyclohexane carboxamide derivatives and pharmaceutical compositions thereof
HK1012336B (en)	2001-11-30	Benzimidazole derivatives, process for their preparation and application