HRP950435A2 - New n-benzylindol and benzopyrazol derivatives with anti-asthmatic, anti-allergic, anti-inflammatory and immunomodulating effects - Google Patents

New n-benzylindol and benzopyrazol derivatives with anti-asthmatic, anti-allergic, anti-inflammatory and immunomodulating effects Download PDF

Info

Publication number: HRP950435A2
Authority: HR; Croatia
Prior art keywords: pyridin; image; indol; alkyl; compounds
Prior art date: 1994-08-03

Application number

HR19511916.9A

Other languages

English (en)

Croatian (hr)

Inventor

Stefan Szelenyi

Original Assignee

Stefan Szelenyi

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.)

1994-08-03

Filing date

1995-08-02

Publication date

1997-12-31

1995-03-31 Priority claimed from DE19511916A external-priority patent/DE19511916A1/de

1995-08-02 Application filed by Stefan Szelenyi filed Critical Stefan Szelenyi

1997-12-31 Publication of HRP950435A2 publication Critical patent/HRP950435A2/hr

Links

230000001088 anti-asthma Effects 0.000 title claims description 4
230000003110 anti-inflammatory effect Effects 0.000 title claims description 4
230000003266 anti-allergic effect Effects 0.000 title claims description 3
239000000924 antiasthmatic agent Substances 0.000 title claims description 3
230000002519 immonomodulatory effect Effects 0.000 title claims description 3
BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical class C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 title description 3
150000001875 compounds Chemical class 0.000 claims description 98
-1 2-quinolyl Chemical group 0.000 claims description 65
239000000203 mixture Substances 0.000 claims description 31
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 30
239000002904 solvent Substances 0.000 claims description 26
238000007792 addition Methods 0.000 claims description 25
239000002253 acid Substances 0.000 claims description 24
150000003839 salts Chemical class 0.000 claims description 22
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 20
125000000217 alkyl group Chemical group 0.000 claims description 20
238000000034 method Methods 0.000 claims description 20
229910052739 hydrogen Inorganic materials 0.000 claims description 18
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 16
238000006243 chemical reaction Methods 0.000 claims description 16
229910052736 halogen Inorganic materials 0.000 claims description 15
150000002367 halogens Chemical group 0.000 claims description 15
239000001257 hydrogen Substances 0.000 claims description 15
239000000126 substance Substances 0.000 claims description 15
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
239000002585 base Substances 0.000 claims description 11
125000004433 nitrogen atom Chemical group N* 0.000 claims description 11
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
125000000623 heterocyclic group Chemical group 0.000 claims description 10
125000000814 indol-3-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C([*])C2=C1[H] 0.000 claims description 10
229910052757 nitrogen Inorganic materials 0.000 claims description 10
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
125000003118 aryl group Chemical group 0.000 claims description 8
238000004519 manufacturing process Methods 0.000 claims description 8
239000003814 drug Substances 0.000 claims description 7
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 6
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 6
VQDZDAUWYCUULB-UHFFFAOYSA-N 2-[1-[(4-fluorophenyl)methyl]indol-3-yl]-n-pyridin-4-ylacetamide Chemical compound C1=CC(F)=CC=C1CN1C2=CC=CC=C2C(CC(=O)NC=2C=CN=CC=2)=C1 VQDZDAUWYCUULB-UHFFFAOYSA-N 0.000 claims description 6
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
239000003795 chemical substances by application Substances 0.000 claims description 6
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 5
229940079593 drug Drugs 0.000 claims description 5
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 4
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
125000003277 amino group Chemical group 0.000 claims description 4
125000003710 aryl alkyl group Chemical group 0.000 claims description 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 4
239000003054 catalyst Substances 0.000 claims description 4
239000003153 chemical reaction reagent Substances 0.000 claims description 4
125000001072 heteroaryl group Chemical group 0.000 claims description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims description 4
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
125000003545 alkoxy group Chemical group 0.000 claims description 3
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
229910052799 carbon Inorganic materials 0.000 claims description 3
239000003638 chemical reducing agent Substances 0.000 claims description 3
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 3
229910052760 oxygen Inorganic materials 0.000 claims description 3
229920006395 saturated elastomer Polymers 0.000 claims description 3
229910052717 sulfur Inorganic materials 0.000 claims description 3
125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims description 2
125000005862 (C1-C6)alkanoyl group Chemical group 0.000 claims description 2
VWJWQQFRTOFGIO-UHFFFAOYSA-N 2-(1-ethylindol-3-yl)-n-pyridin-4-ylacetamide Chemical compound C12=CC=CC=C2N(CC)C=C1CC(=O)NC1=CC=NC=C1 VWJWQQFRTOFGIO-UHFFFAOYSA-N 0.000 claims description 2
WATRTCKNYDTCHZ-UHFFFAOYSA-N 2-(5-propan-2-yl-1h-indol-3-yl)-n-pyridin-4-ylacetamide Chemical compound C12=CC(C(C)C)=CC=C2NC=C1CC(=O)NC1=CC=NC=C1 WATRTCKNYDTCHZ-UHFFFAOYSA-N 0.000 claims description 2
HIXVJZXTZKCSCJ-UHFFFAOYSA-N 2-(6-methoxy-3-nitropyridin-2-yl)-1-methyl-1,3,4,9-tetrahydropyrido[3,4-b]indole Chemical compound COC1=CC=C([N+]([O-])=O)C(N2C(C3=C(C4=CC=CC=C4N3)CC2)C)=N1 HIXVJZXTZKCSCJ-UHFFFAOYSA-N 0.000 claims description 2
ZFCDLWUKULWPJT-UHFFFAOYSA-N 2-[1-[(4-fluorophenyl)methyl]-6-hydroxyindol-3-yl]-n-pyridin-4-ylacetamide Chemical compound C=1N(CC=2C=CC(F)=CC=2)C2=CC(O)=CC=C2C=1CC(=O)NC1=CC=NC=C1 ZFCDLWUKULWPJT-UHFFFAOYSA-N 0.000 claims description 2
125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 2
MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 2
125000003435 aroyl group Chemical group 0.000 claims description 2
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims description 2
230000027326 copulation Effects 0.000 claims description 2
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
125000006627 ethoxycarbonylamino group Chemical group 0.000 claims description 2
HYJCTJQYIGRCCN-UHFFFAOYSA-N ethyl n-[2-[2-(1-benzylindol-3-yl)ethylamino]-6-methoxypyridin-3-yl]carbamate Chemical compound CCOC(=O)NC1=CC=C(OC)N=C1NCCC(C1=CC=CC=C11)=CN1CC1=CC=CC=C1 HYJCTJQYIGRCCN-UHFFFAOYSA-N 0.000 claims description 2
YWFWERPETPNBPP-UHFFFAOYSA-N ethyl n-[2-[3-[1-[(4-fluorophenyl)methyl]indol-3-yl]propylamino]-6-methoxypyridin-3-yl]carbamate Chemical class CCOC(=O)NC1=CC=C(OC)N=C1NCCCC(C1=CC=CC=C11)=CN1CC1=CC=C(F)C=C1 YWFWERPETPNBPP-UHFFFAOYSA-N 0.000 claims description 2
229910052731 fluorine Inorganic materials 0.000 claims description 2
239000011737 fluorine Substances 0.000 claims description 2
JOWWRFRCMDFLJB-UHFFFAOYSA-N n-[2-[1-[(4-fluorophenyl)methyl]indol-3-yl]ethyl]pyridin-2-amine Chemical compound C1=CC(F)=CC=C1CN1C2=CC=CC=C2C(CCNC=2N=CC=CC=2)=C1 JOWWRFRCMDFLJB-UHFFFAOYSA-N 0.000 claims description 2
QVUSHJMYWHAFRZ-UHFFFAOYSA-N n-[3-(1-methylindol-3-yl)propyl]pyridin-4-amine Chemical compound C12=CC=CC=C2N(C)C=C1CCCNC1=CC=NC=C1 QVUSHJMYWHAFRZ-UHFFFAOYSA-N 0.000 claims description 2
SPVVKMDHVOAWHC-UHFFFAOYSA-N n-[3-[1-[(4-fluorophenyl)methyl]indol-3-yl]propyl]pyridin-3-amine Chemical compound C1=CC(F)=CC=C1CN1C2=CC=CC=C2C(CCCNC=2C=NC=CC=2)=C1 SPVVKMDHVOAWHC-UHFFFAOYSA-N 0.000 claims description 2
125000001624 naphthyl group Chemical group 0.000 claims description 2
125000004193 piperazinyl group Chemical group 0.000 claims description 2
125000003386 piperidinyl group Chemical group 0.000 claims description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 2
125000003396 thiol group Chemical group [H]S* 0.000 claims description 2
125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 2
JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 2
239000003085 diluting agent Substances 0.000 claims 4
HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 claims 3
230000008878 coupling Effects 0.000 claims 2
238000010168 coupling process Methods 0.000 claims 2
238000005859 coupling reaction Methods 0.000 claims 2
HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims 1
239000000969 carrier Substances 0.000 claims 1
239000007822 coupling agent Substances 0.000 claims 1
239000003937 drug carrier Substances 0.000 claims 1
125000001033 ether group Chemical group 0.000 claims 1
XFAIHZDUZNCFMN-UHFFFAOYSA-N n-[2-(1-benzylindol-3-yl)ethyl]pyridin-4-amine Chemical compound C=1C=NC=CC=1NCCC(C1=CC=CC=C11)=CN1CC1=CC=CC=C1 XFAIHZDUZNCFMN-UHFFFAOYSA-N 0.000 claims 1
CHKOUGKFBKDLRC-UHFFFAOYSA-N n-[2-[1-[(4-fluorophenyl)methyl]indol-3-yl]ethyl]pyridin-3-amine Chemical compound C1=CC(F)=CC=C1CN1C2=CC=CC=C2C(CCNC=2C=NC=CC=2)=C1 CHKOUGKFBKDLRC-UHFFFAOYSA-N 0.000 claims 1
YSBIMMXFUCTECO-UHFFFAOYSA-N n-[2-[1-[(4-fluorophenyl)methyl]indol-3-yl]ethyl]pyridin-4-amine Chemical compound C1=CC(F)=CC=C1CN1C2=CC=CC=C2C(CCNC=2C=CN=CC=2)=C1 YSBIMMXFUCTECO-UHFFFAOYSA-N 0.000 claims 1
239000008024 pharmaceutical diluent Substances 0.000 claims 1
239000000546 pharmaceutical excipient Substances 0.000 claims 1
239000000825 pharmaceutical preparation Substances 0.000 claims 1
125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims 1
125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims 1
125000005493 quinolyl group Chemical group 0.000 claims 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 82
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 48
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 41
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 32
238000003786 synthesis reaction Methods 0.000 description 30
230000015572 biosynthetic process Effects 0.000 description 29
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 24
230000033228 biological regulation Effects 0.000 description 23
239000000243 solution Substances 0.000 description 21
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 19
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
238000002844 melting Methods 0.000 description 16
230000008018 melting Effects 0.000 description 16
238000003756 stirring Methods 0.000 description 16
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 14
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 13
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 13
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 11
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
210000004027 cell Anatomy 0.000 description 11
238000004440 column chromatography Methods 0.000 description 11
239000000741 silica gel Substances 0.000 description 11
229910002027 silica gel Inorganic materials 0.000 description 11
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 10
238000010992 reflux Methods 0.000 description 10
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 9
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
238000009835 boiling Methods 0.000 description 9
239000003480 eluent Substances 0.000 description 9
125000004494 ethyl ester group Chemical group 0.000 description 9
239000002244 precipitate Substances 0.000 description 9
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 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 8
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 8
239000012074 organic phase Substances 0.000 description 8
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 7
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
238000006482 condensation reaction Methods 0.000 description 7
238000001816 cooling Methods 0.000 description 7
239000003208 petroleum Substances 0.000 description 7
229910000027 potassium carbonate Inorganic materials 0.000 description 7
239000000725 suspension Substances 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
150000002168 ethanoic acid esters Chemical class 0.000 description 6
150000002475 indoles Chemical class 0.000 description 6
239000003960 organic solvent Substances 0.000 description 6
235000015320 potassium carbonate Nutrition 0.000 description 6
238000002360 preparation method Methods 0.000 description 6
235000002639 sodium chloride Nutrition 0.000 description 6
235000011121 sodium hydroxide Nutrition 0.000 description 6
125000001424 substituent group Chemical group 0.000 description 6
BDNKZNFMNDZQMI-UHFFFAOYSA-N 1,3-diisopropylcarbodiimide Chemical compound CC(C)N=C=NC(C)C BDNKZNFMNDZQMI-UHFFFAOYSA-N 0.000 description 5
DVRGUTNVDGIKTP-UHFFFAOYSA-N 2-chloro-6-methoxy-3-nitropyridine Chemical compound COC1=CC=C([N+]([O-])=O)C(Cl)=N1 DVRGUTNVDGIKTP-UHFFFAOYSA-N 0.000 description 5
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 5
241001465754 Metazoa Species 0.000 description 5
BGRWYRAHAFMIBJ-UHFFFAOYSA-N diisopropylcarbodiimide Natural products CC(C)NC(=O)NC(C)C BGRWYRAHAFMIBJ-UHFFFAOYSA-N 0.000 description 5
238000001704 evaporation Methods 0.000 description 5
230000008020 evaporation Effects 0.000 description 5
229960001340 histamine Drugs 0.000 description 5
230000005764 inhibitory process Effects 0.000 description 5
239000012280 lithium aluminium hydride Substances 0.000 description 5
239000012299 nitrogen atmosphere Substances 0.000 description 5
229940080818 propionamide Drugs 0.000 description 5
MHNYJYPQHXBYTH-UHFFFAOYSA-N 1-[(4-chlorophenyl)methyl]-3-(1-methylazepan-4-yl)oxyindazole Chemical compound C1CN(C)CCCC1OC(C1=CC=CC=C11)=NN1CC1=CC=C(Cl)C=C1 MHNYJYPQHXBYTH-UHFFFAOYSA-N 0.000 description 4
CFTOTSJVQRFXOF-UHFFFAOYSA-N 2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole Chemical compound N1C2=CC=CC=C2C2=C1CNCC2 CFTOTSJVQRFXOF-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
102000000743 Interleukin-5 Human genes 0.000 description 4
108010002616 Interleukin-5 Proteins 0.000 description 4
102000015696 Interleukins Human genes 0.000 description 4
108010063738 Interleukins Proteins 0.000 description 4
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
150000001408 amides Chemical class 0.000 description 4
BYFMCKSPFYVMOU-UHFFFAOYSA-N bendazac Chemical compound C12=CC=CC=C2C(OCC(=O)O)=NN1CC1=CC=CC=C1 BYFMCKSPFYVMOU-UHFFFAOYSA-N 0.000 description 4
238000009833 condensation Methods 0.000 description 4
230000005494 condensation Effects 0.000 description 4
239000013078 crystal Substances 0.000 description 4
238000000921 elemental analysis Methods 0.000 description 4
238000010828 elution Methods 0.000 description 4
210000003979 eosinophil Anatomy 0.000 description 4
150000002431 hydrogen Chemical class 0.000 description 4
238000000338 in vitro Methods 0.000 description 4
CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 4
QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
238000001953 recrystallisation Methods 0.000 description 4
239000012279 sodium borohydride Substances 0.000 description 4
229910000033 sodium borohydride Inorganic materials 0.000 description 4
ZXLDQJLIBNPEFJ-UHFFFAOYSA-N tetrahydro-beta-carboline Natural products C1CNC(C)C2=C1C1=CC=C(OC)C=C1N2 ZXLDQJLIBNPEFJ-UHFFFAOYSA-N 0.000 description 4
APJYDQYYACXCRM-UHFFFAOYSA-N tryptamine Chemical compound C1=CC=C2C(CCN)=CNC2=C1 APJYDQYYACXCRM-UHFFFAOYSA-N 0.000 description 4
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239000012298 atmosphere Substances 0.000 description 1
208000010668 atopic eczema Diseases 0.000 description 1
DCBDOYDVQJVXOH-UHFFFAOYSA-N azane;1h-indole Chemical compound N.C1=CC=C2NC=CC2=C1 DCBDOYDVQJVXOH-UHFFFAOYSA-N 0.000 description 1
229960004574 azelastine Drugs 0.000 description 1
RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
229960005149 bendazac Drugs 0.000 description 1
150000001556 benzimidazoles Chemical class 0.000 description 1
AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
239000008280 blood Substances 0.000 description 1
230000017531 blood circulation Effects 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
230000007885 bronchoconstriction Effects 0.000 description 1
KMGBZBJJOKUPIA-UHFFFAOYSA-N butyl iodide Chemical compound CCCCI KMGBZBJJOKUPIA-UHFFFAOYSA-N 0.000 description 1
239000001110 calcium chloride Substances 0.000 description 1
235000011148 calcium chloride Nutrition 0.000 description 1
229910001628 calcium chloride Inorganic materials 0.000 description 1
239000004202 carbamide Substances 0.000 description 1
150000001721 carbon Chemical group 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
235000015165 citric acid Nutrition 0.000 description 1
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid group Chemical class C(CC(O)(C(=O)O)CC(=O)O)(=O)O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
230000034994 death Effects 0.000 description 1
231100000517 death Toxicity 0.000 description 1
239000002027 dichloromethane extract Substances 0.000 description 1
239000002934 diuretic Substances 0.000 description 1
229940030606 diuretics Drugs 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000003073 embolic effect Effects 0.000 description 1
VEUUMBGHMNQHGO-UHFFFAOYSA-N ethyl chloroacetate Chemical compound CCOC(=O)CCl VEUUMBGHMNQHGO-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
AKHRHLWPJFPVPX-UHFFFAOYSA-N ethyl n-[2-[2-(1h-indol-3-yl)ethylamino]-6-methoxypyridin-3-yl]carbamate Chemical compound CCOC(=O)NC1=CC=C(OC)N=C1NCCC1=CNC2=CC=CC=C12 AKHRHLWPJFPVPX-UHFFFAOYSA-N 0.000 description 1
CRIIGUDNUNZTBP-UHFFFAOYSA-N ethyl n-[2-[2-(5-chloro-1h-indol-3-yl)ethylamino]-6-methoxypyridin-3-yl]carbamate Chemical compound CCOC(=O)NC1=CC=C(OC)N=C1NCCC1=CNC2=CC=C(Cl)C=C12 CRIIGUDNUNZTBP-UHFFFAOYSA-N 0.000 description 1
SOUOTNBOQKNIIC-UHFFFAOYSA-N ethyl n-[2-[3-(1h-indol-3-yl)propylamino]-6-methoxypyridin-3-yl]carbamate Chemical compound CCOC(=O)NC1=CC=C(OC)N=C1NCCCC1=CNC2=CC=CC=C12 SOUOTNBOQKNIIC-UHFFFAOYSA-N 0.000 description 1
JBTWTOLEJMGAOX-UHFFFAOYSA-N ethyl n-[2-amino-6-(1,3,4,9-tetrahydropyrido[3,4-b]indol-2-yl)pyridin-3-yl]carbamate Chemical compound N1=C(N)C(NC(=O)OCC)=CC=C1N1CC(NC=2C3=CC=CC=2)=C3CC1 JBTWTOLEJMGAOX-UHFFFAOYSA-N 0.000 description 1
PTFNGDMGEGUGAB-UHFFFAOYSA-N ethyl n-[2-amino-6-[2-(1-methylindol-3-yl)ethylamino]pyridin-3-yl]carbamate Chemical compound N1=C(N)C(NC(=O)OCC)=CC=C1NCCC1=CN(C)C2=CC=CC=C12 PTFNGDMGEGUGAB-UHFFFAOYSA-N 0.000 description 1
WYMRJCOUTNIINX-UHFFFAOYSA-N ethyl n-[2-amino-6-[2-(1h-indol-3-yl)ethylamino]pyridin-3-yl]carbamate Chemical compound N1=C(N)C(NC(=O)OCC)=CC=C1NCCC1=CNC2=CC=CC=C12 WYMRJCOUTNIINX-UHFFFAOYSA-N 0.000 description 1
YWUVDTBNEIHUNJ-UHFFFAOYSA-N ethyl n-[2-amino-6-[3-[1-[(4-fluorophenyl)methyl]indol-3-yl]propylamino]pyridin-3-yl]carbamate Chemical compound N1=C(N)C(NC(=O)OCC)=CC=C1NCCCC(C1=CC=CC=C11)=CN1CC1=CC=C(F)C=C1 YWUVDTBNEIHUNJ-UHFFFAOYSA-N 0.000 description 1
NUPSQXDLGJNYNC-UHFFFAOYSA-N ethyl n-[2-amino-6-[4-[2-(1h-indol-3-yl)propanoylamino]piperidin-1-yl]pyridin-3-yl]carbamate Chemical compound N1=C(N)C(NC(=O)OCC)=CC=C1N1CCC(NC(=O)C(C)C=2C3=CC=CC=C3NC=2)CC1 NUPSQXDLGJNYNC-UHFFFAOYSA-N 0.000 description 1
QJEWLJYDWRLICY-UHFFFAOYSA-N ethyl n-[6-amino-2-[2-(2-methyl-1h-indol-3-yl)ethylamino]pyridin-3-yl]carbamate Chemical compound CCOC(=O)NC1=CC=C(N)N=C1NCCC1=C(C)NC2=CC=CC=C12 QJEWLJYDWRLICY-UHFFFAOYSA-N 0.000 description 1
RFUSWYQGSISAFL-UHFFFAOYSA-N ethyl n-[6-methoxy-2-(1,3,4,9-tetrahydropyrido[3,4-b]indol-2-yl)pyridin-3-yl]carbamate Chemical compound CCOC(=O)NC1=CC=C(OC)N=C1N1CC(NC=2C3=CC=CC=2)=C3CC1 RFUSWYQGSISAFL-UHFFFAOYSA-N 0.000 description 1
FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000000284 extract Substances 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
239000011521 glass Substances 0.000 description 1
235000012208 gluconic acid Nutrition 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
210000002443 helper t lymphocyte Anatomy 0.000 description 1
125000004475 heteroaralkyl group Chemical group 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
125000001041 indolyl group Chemical group 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
229940028885 interleukin-4 Drugs 0.000 description 1
229940100602 interleukin-5 Drugs 0.000 description 1
239000011630 iodine Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
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 1
TWXDDNPPQUTEOV-FVGYRXGTSA-N methamphetamine hydrochloride Chemical compound Cl.CN[C@@H](C)CC1=CC=CC=C1 TWXDDNPPQUTEOV-FVGYRXGTSA-N 0.000 description 1
JPYXJYNGXVQKMU-UHFFFAOYSA-N methyl 6-[[2-[1-[(4-fluorophenyl)methyl]indazol-3-yl]oxyacetyl]amino]pyridine-3-carboxylate Chemical compound N1=CC(C(=O)OC)=CC=C1NC(=O)COC(C1=CC=CC=C11)=NN1CC1=CC=C(F)C=C1 JPYXJYNGXVQKMU-UHFFFAOYSA-N 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000011707 mineral Substances 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
FGMNXOSOHCYKAK-UHFFFAOYSA-N n-(2,6-dimethyl-1h-pyridin-2-yl)-2-[1-[(4-fluorophenyl)methyl]indol-3-yl]acetamide Chemical compound N1C(C)=CC=CC1(C)NC(=O)CC(C1=CC=CC=C11)=CN1CC1=CC=C(F)C=C1 FGMNXOSOHCYKAK-UHFFFAOYSA-N 0.000 description 1
FSBUNHCGZUJZND-UHFFFAOYSA-N n-(4,6-dimethylpyridin-2-yl)-2-(1-ethylindol-3-yl)acetamide Chemical compound C12=CC=CC=C2N(CC)C=C1CC(=O)NC1=CC(C)=CC(C)=N1 FSBUNHCGZUJZND-UHFFFAOYSA-N 0.000 description 1
CNYXPKITAYXBOQ-UHFFFAOYSA-N n-(6-aminopyridin-2-yl)-2-[1-[(4-chlorophenyl)methyl]indazol-3-yl]oxyacetamide Chemical compound NC1=CC=CC(NC(=O)COC=2C3=CC=CC=C3N(CC=3C=CC(Cl)=CC=3)N=2)=N1 CNYXPKITAYXBOQ-UHFFFAOYSA-N 0.000 description 1
SEDHJBTUFZSSSO-UHFFFAOYSA-N n-[1-(6-amino-5-nitropyridin-2-yl)piperidin-4-yl]-2-(1h-indol-3-yl)acetamide Chemical compound C1=C([N+]([O-])=O)C(N)=NC(N2CCC(CC2)NC(=O)CC=2C3=CC=CC=C3NC=2)=C1 SEDHJBTUFZSSSO-UHFFFAOYSA-N 0.000 description 1
AFZRZBYXDLZBSG-UHFFFAOYSA-N n-[1-(6-amino-5-nitropyridin-2-yl)piperidin-4-yl]-3-(1h-indol-3-yl)propanamide Chemical compound C1=C([N+]([O-])=O)C(N)=NC(N2CCC(CC2)NC(=O)CCC=2C3=CC=CC=C3NC=2)=C1 AFZRZBYXDLZBSG-UHFFFAOYSA-N 0.000 description 1
CWVUFXZPSYSMNF-UHFFFAOYSA-N n-[2-(1-butylindol-3-yl)ethyl]pyridin-4-amine Chemical compound C12=CC=CC=C2N(CCCC)C=C1CCNC1=CC=NC=C1 CWVUFXZPSYSMNF-UHFFFAOYSA-N 0.000 description 1
VLJASCDYSLFFOH-UHFFFAOYSA-N n-[2-(5-chloro-1h-indol-3-yl)ethyl]-6-methoxy-3-nitropyridin-2-amine Chemical compound COC1=CC=C([N+]([O-])=O)C(NCCC=2C3=CC(Cl)=CC=C3NC=2)=N1 VLJASCDYSLFFOH-UHFFFAOYSA-N 0.000 description 1
BEBSCDUSERCGRS-UHFFFAOYSA-N n-[2-[1-[(2-fluorophenyl)methyl]indol-3-yl]ethyl]pyridin-4-amine Chemical compound FC1=CC=CC=C1CN1C2=CC=CC=C2C(CCNC=2C=CN=CC=2)=C1 BEBSCDUSERCGRS-UHFFFAOYSA-N 0.000 description 1
DUOYBHMHXRJMMY-UHFFFAOYSA-N n-[2-[1-[(4-chlorophenyl)methyl]indol-3-yl]ethyl]pyridin-4-amine Chemical compound C1=CC(Cl)=CC=C1CN1C2=CC=CC=C2C(CCNC=2C=CN=CC=2)=C1 DUOYBHMHXRJMMY-UHFFFAOYSA-N 0.000 description 1
LVSNSAFZVBOFJS-UHFFFAOYSA-N n-[2-[1-[(4-fluorophenyl)methyl]indol-3-yl]ethyl]-6-methoxy-3-nitropyridin-2-amine Chemical compound COC1=CC=C([N+]([O-])=O)C(NCCC=2C3=CC=CC=C3N(CC=3C=CC(F)=CC=3)C=2)=N1 LVSNSAFZVBOFJS-UHFFFAOYSA-N 0.000 description 1
HPFZEFGOOBWZJR-UHFFFAOYSA-N n-[3-(1-methylindol-3-yl)propyl]pyridin-3-amine Chemical compound C12=CC=CC=C2N(C)C=C1CCCNC1=CC=CN=C1 HPFZEFGOOBWZJR-UHFFFAOYSA-N 0.000 description 1
OYVWLEYQNBYZEI-UHFFFAOYSA-N n-[3-(1h-indol-3-yl)propyl]-6-methoxy-3-nitropyridin-2-amine Chemical compound COC1=CC=C([N+]([O-])=O)C(NCCCC=2C3=CC=CC=C3NC=2)=N1 OYVWLEYQNBYZEI-UHFFFAOYSA-N 0.000 description 1
QQMVQXLLQJYCOE-UHFFFAOYSA-N n-[3-[1-[(4-fluorophenyl)methyl]indol-3-yl]propyl]pyridin-4-amine Chemical compound C1=CC(F)=CC=C1CN1C2=CC=CC=C2C(CCCNC=2C=CN=CC=2)=C1 QQMVQXLLQJYCOE-UHFFFAOYSA-N 0.000 description 1
FGUXMBBACOZGNY-UHFFFAOYSA-N n-[4-[1-[(4-fluorophenyl)methyl]indol-3-yl]butyl]pyridin-4-amine Chemical compound C1=CC(F)=CC=C1CN1C2=CC=CC=C2C(CCCCNC=2C=CN=CC=2)=C1 FGUXMBBACOZGNY-UHFFFAOYSA-N 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
MHDWYHZKGZXNPU-UHFFFAOYSA-N n-pyridin-4-yl-2-[1-[[3-(trifluoromethyl)phenyl]methyl]indol-3-yl]acetamide Chemical compound FC(F)(F)C1=CC=CC(CN2C3=CC=CC=C3C(CC(=O)NC=3C=CN=CC=3)=C2)=C1 MHDWYHZKGZXNPU-UHFFFAOYSA-N 0.000 description 1
MCSAJNNLRCFZED-UHFFFAOYSA-N nitroethane Chemical compound CC[N+]([O-])=O MCSAJNNLRCFZED-UHFFFAOYSA-N 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
229960002275 pentobarbital sodium Drugs 0.000 description 1
125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
210000003200 peritoneal cavity Anatomy 0.000 description 1
239000012071 phase Substances 0.000 description 1
KSPBOCRLZHYULL-UHFFFAOYSA-N phenyl n-[2-[2-(1h-indol-3-yl)ethylamino]-6-methoxypyridin-3-yl]carbamate Chemical compound C=1NC2=CC=CC=C2C=1CCNC1=NC(OC)=CC=C1NC(=O)OC1=CC=CC=C1 KSPBOCRLZHYULL-UHFFFAOYSA-N 0.000 description 1
125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 description 1
210000003281 pleural cavity Anatomy 0.000 description 1
229940093956 potassium carbonate Drugs 0.000 description 1
235000011181 potassium carbonates Nutrition 0.000 description 1
CUQOHAYJWVTKDE-UHFFFAOYSA-N potassium;butan-1-olate Chemical compound [K+].CCCC[O-] CUQOHAYJWVTKDE-UHFFFAOYSA-N 0.000 description 1
239000000843 powder Substances 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
239000000047 product Substances 0.000 description 1
FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
239000002516 radical scavenger Substances 0.000 description 1
239000002464 receptor antagonist Substances 0.000 description 1
229940044551 receptor antagonist Drugs 0.000 description 1
230000025078 regulation of biosynthetic process Effects 0.000 description 1
238000007790 scraping Methods 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000003369 serotonin 5-HT3 receptor antagonist Substances 0.000 description 1
238000010898 silica gel chromatography Methods 0.000 description 1
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
235000017550 sodium carbonate Nutrition 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 1
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
238000012453 sprague-dawley rat model Methods 0.000 description 1
239000007929 subcutaneous injection Substances 0.000 description 1
238000001308 synthesis method Methods 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
125000005323 thioketone group Chemical group 0.000 description 1
210000001519 tissue Anatomy 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1

Classifications

- 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
- C07D403/02—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 two hetero rings
- C07D403/12—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 two hetero rings linked by a chain containing hetero atoms as chain links
- 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
- 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
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/04—Immunostimulants
- 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
- 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
- C07D401/12—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 linked by a chain containing hetero atoms as chain links
- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Public Health (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Veterinary Medicine (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Immunology (AREA)
Pulmonology (AREA)
Pain & Pain Management (AREA)
Rheumatology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Indole Compounds (AREA)

HR19511916.9A 1994-08-03 1995-08-02 New n-benzylindol and benzopyrazol derivatives with anti-asthmatic, anti-allergic, anti-inflammatory and immunomodulating effects HRP950435A2 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE4427393		1994-08-03
DE19511916A DE19511916A1 (de)	1994-08-03	1995-03-31	Neue N-Benzylindol- und Benzopyrazol-Derivate mit antiasthmatischer, antiallergischer, entzündungshemmender und immunmodulierender Wirkung

Publications (1)

Publication Number	Publication Date
HRP950435A2 true HRP950435A2 (en)	1997-12-31

Family

ID=25938901

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
HR19511916.9A HRP950435A2 (en)	1994-08-03	1995-08-02	New n-benzylindol and benzopyrazol derivatives with anti-asthmatic, anti-allergic, anti-inflammatory and immunomodulating effects

Country Status (13)

Country	Link
US (1)	US5965582A (fr)
EP (1)	EP0775131A2 (fr)
JP (1)	JPH10503501A (fr)
AU (1)	AU3162695A (fr)
CA (1)	CA2195850A1 (fr)
EG (1)	EG21559A (fr)
FI (1)	FI971334A0 (fr)
HR (1)	HRP950435A2 (fr)
IL (1)	IL114795A (fr)
NO (1)	NO970412L (fr)
TR (1)	TR199500952A2 (fr)
TW (1)	TW434227B (fr)
WO (1)	WO1996004266A2 (fr)

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1995
- 1995-07-20 JP JP8506137A patent/JPH10503501A/ja active Pending
- 1995-07-20 US US08/776,616 patent/US5965582A/en not_active Expired - Fee Related
- 1995-07-20 EP EP95927679A patent/EP0775131A2/fr not_active Withdrawn
- 1995-07-20 WO PCT/EP1995/002867 patent/WO1996004266A2/fr not_active Ceased
- 1995-07-20 CA CA002195850A patent/CA2195850A1/fr not_active Abandoned
- 1995-07-20 FI FI971334A patent/FI971334A0/fi active IP Right Revival
- 1995-07-20 AU AU31626/95A patent/AU3162695A/en not_active Abandoned
- 1995-07-26 TW TW084107752A patent/TW434227B/zh not_active IP Right Cessation
- 1995-08-01 IL IL11479595A patent/IL114795A/xx not_active IP Right Cessation
- 1995-08-01 EG EG64495A patent/EG21559A/xx active
- 1995-08-02 HR HR19511916.9A patent/HRP950435A2/hr not_active Application Discontinuation
- 1995-08-03 TR TR95/00952A patent/TR199500952A2/xx unknown
1997
- 1997-01-30 NO NO970412A patent/NO970412L/no not_active Application Discontinuation

Also Published As

Publication number	Publication date
FI971334L (fi)	1997-04-01
WO1996004266A2 (fr)	1996-02-15
NO970412D0 (no)	1997-01-30
FI971334A7 (fi)	1997-04-01
CA2195850A1 (fr)	1996-02-15
IL114795A0 (en)	1995-12-08
FI971334A0 (fi)	1997-04-01
US5965582A (en)	1999-10-12
NO970412L (no)	1997-02-27
EP0775131A2 (fr)	1997-05-28
EG21559A (en)	2001-12-31
TR199500952A2 (tr)	1996-07-21
TW434227B (en)	2001-05-16
WO1996004266A3 (fr)	1996-05-17
IL114795A (en)	1999-11-30
JPH10503501A (ja)	1998-03-31
AU3162695A (en)	1996-03-04

Legal Events

Date	Code	Title	Description
1997-12-31	A1OB	Publication of a patent application
1998-04-09	AIPI	Request for the grant of a patent on the basis of a substantive examination of a patent application
2001-08-14	ODRP	Renewal fee for the maintenance of a patent	Payment date: 20010814 Year of fee payment: 7
2007-01-19	ODBI	Application refused

Publication	Publication Date	Title
HRP950435A2 (en)	1997-12-31	New n-benzylindol and benzopyrazol derivatives with anti-asthmatic, anti-allergic, anti-inflammatory and immunomodulating effects
JP2788551B2 (ja)	1998-08-20	５−アリールインドール誘導体およびセロトニン（５−ｈｔ▲下１▼）作用薬としてのそれらの用途
AU761574B2 (en)	2003-06-05	3-azabicyclo(3.1.0.) hexane derivatives as opiate receptors ligands
US5834493A (en)	1998-11-10	Indole derivatives as 5-HT1A and/or 5-HT2 ligands
JP3218037B2 (ja)	2001-10-15	喘息および呼吸器官の炎症の治療に有用なヘテロサイクリックアミン類
EA000829B1 (ru)	2000-04-24	Антагонисты гонадотропин-высвобождающего фактора
US5981525A (en)	1999-11-09	Indole derivatives useful in the treatment of osteoporosis
US5866589A (en)	1999-02-02	Alkyl substituted piperadinyl and piperazinyl anti-AIDS compounds
CA2399791A1 (fr)	2001-08-16	Modulateurs de recepteurs aux cannabinoides, leurs procedes de preparation et utilisations de modulateurs de recepteurs aux cannabinoides pour le traitement de maladies respiratoires et non respiratoires
JPH06271571A (ja)	1994-09-27	インドール、インダゾール及びベンズイソオキサゾール化合物、それらの製法およびそれらを含有する製薬組成物
PT95899A (pt)	1991-09-13	Processo para a preparacao de derivados indole
US6903117B2 (en)	2005-06-07	Indole derivatives for the treatment of osteoporosis
WO1998001428A1 (fr)	1998-01-15	AMIDINOINDOLES, AMIDINOAZOLES ET LEURS ANALOGUES AGISSANT EN TANT QU'INHIBITEURS DU FACTEUR Xa ET DE LA THROMBINE
NZ230068A (en)	1991-07-26	Indazole-3-carboxylic acid esters and amides of diaza compounds having 6,7, or 8 ring members: preparatory processes and pharmaceutical compositions
NO166862B (no)	1991-06-03	Analogifremgangsmaate for fremstilling av terapeutisk aktive 1,8-nafthyridinderivater og deres salter, solvater, hydrater og estere.
PL172232B1 (pl)	1997-08-29	Pochodne acyloaminoindolu PL PL PL PL PL PL PL PL
CZ16994A3 (en)	1994-06-15	Heterocyclic compounds and pharmaceutical preparations in which they are comprised
JPH06505979A (ja)	1994-07-07	ベンゾフラン誘導体
US5049679A (en)	1991-09-17	Carboxamide derivatives
JPH07500345A (ja)	1995-01-12	アンジオテンシン２拮抗剤としてのピリミドシクロアルカン類
HUT64320A (en)	1993-12-28	Process for production antiallergic imidazole derivatives and pharmaceutical preparations containing these compounds
DE3914764A1 (de)	1990-11-08	Maleinimid-derivate und deren verwendung als arzneimittel
HUT60477A (en)	1992-09-28	Process for producing 4-pyrimidinone derivatives and pharmaceutical compositions comprising such compounds as active ingredient
AU2004200420A1 (en)	2004-09-30	Inhibitor of cyclooxygenase
FR2944792A1 (fr)	2010-10-29	Derives de 1h-pyrazolo[4,3-c]isoquinoleines, leur preparation et leur application en therapeutique