IL93776A - Antilateral substances of type 1,4 - pretty, fresh and molten tetracyclic diazepines and pharmaceutical preparations containing them - Google Patents

Antilateral substances of type 1,4 - pretty, fresh and molten tetracyclic diazepines and pharmaceutical preparations containing them

Info

Publication number: IL93776A
Authority: IL; Israel
Prior art keywords: methyl; alkyl; pyrid; compound; plc
Prior art date: 1989-03-23

Application number

IL9377690A

Other languages

English (en)

Hebrew (he)

Other versions

IL93776A0 (en

Original Assignee

Pfizer

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.)

1989-03-23

Filing date

1990-03-16

Publication date

1994-10-21

1989-03-23 Priority claimed from GB898906813A external-priority patent/GB8906813D0/en

1989-11-21 Priority claimed from GB898926246A external-priority patent/GB8926246D0/en

1990-03-16 Application filed by Pfizer filed Critical Pfizer

1990-12-23 Publication of IL93776A0 publication Critical patent/IL93776A0/xx

1994-10-21 Publication of IL93776A publication Critical patent/IL93776A/en

Links

239000008194 pharmaceutical composition Substances 0.000 title claims description 5
POXWDTQUDZUOGP-UHFFFAOYSA-N 1h-1,4-diazepine Chemical compound N1C=CC=NC=C1 POXWDTQUDZUOGP-UHFFFAOYSA-N 0.000 title claims 3
239000000043 antiallergic agent Substances 0.000 title description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract description 34
UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims abstract description 23
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 17
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Chemical class COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims abstract description 14
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical class C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims abstract description 8
125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 5
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 4
ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical class C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims abstract description 3
229910052717 sulfur Inorganic materials 0.000 claims abstract description 3
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical class N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims abstract 6
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical class C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims abstract 6
FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical class C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims abstract 4
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical class C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims abstract 3
229930192474 thiophene Chemical class 0.000 claims abstract 3
125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims abstract 2
150000001875 compounds Chemical class 0.000 claims description 162
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 50
-1 perfluoro Chemical group 0.000 claims description 23
125000000217 alkyl group Chemical group 0.000 claims description 22
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 12
SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 claims description 11
229940049706 benzodiazepine Drugs 0.000 claims description 11
229910052739 hydrogen Inorganic materials 0.000 claims description 11
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 8
229910052799 carbon Inorganic materials 0.000 claims description 8
125000003545 alkoxy group Chemical group 0.000 claims description 7
125000005843 halogen group Chemical group 0.000 claims description 7
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
150000003839 salts Chemical class 0.000 claims description 7
125000001424 substituent group Chemical group 0.000 claims description 7
125000003277 amino group Chemical group 0.000 claims description 6
125000002883 imidazolyl group Chemical group 0.000 claims description 6
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 5
125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 4
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
HVAUUPRFYPCOCA-AREMUKBSSA-N 2-O-acetyl-1-O-hexadecyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCCOC[C@@H](OC(C)=O)COP([O-])(=O)OCC[N+](C)(C)C HVAUUPRFYPCOCA-AREMUKBSSA-N 0.000 claims description 3
108010003541 Platelet Activating Factor Proteins 0.000 claims description 3
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
125000004430 oxygen atom Chemical group O* 0.000 claims description 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
125000004076 pyridyl group Chemical group 0.000 claims description 3
OTPDWCMLUKMQNO-UHFFFAOYSA-N 1,2,3,4-tetrahydropyrimidine Chemical group C1NCC=CN1 OTPDWCMLUKMQNO-UHFFFAOYSA-N 0.000 claims description 2
102100025027 E3 ubiquitin-protein ligase TRIM69 Human genes 0.000 claims description 2
101000830203 Homo sapiens E3 ubiquitin-protein ligase TRIM69 Chemical group 0.000 claims description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
239000005864 Sulphur Substances 0.000 claims description 2
239000003085 diluting agent Substances 0.000 claims description 2
239000003814 drug Substances 0.000 claims description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical group C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 claims description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
125000001544 thienyl group Chemical group 0.000 claims description 2
SURVUDPNZQGEJD-UHFFFAOYSA-N 1,4-diazepin-5-one Chemical compound O=C1C=CN=CC=N1 SURVUDPNZQGEJD-UHFFFAOYSA-N 0.000 claims 2
HPYNZHMRTTWQTB-UHFFFAOYSA-N 2,3-dimethylpyridine Chemical compound CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 claims 2
UKGYPSZODXDRJQ-UHFFFAOYSA-N 3-(2-chlorophenyl)-1-methylpyrazole Chemical compound CN1C=CC(C=2C(=CC=CC=2)Cl)=N1 UKGYPSZODXDRJQ-UHFFFAOYSA-N 0.000 claims 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims 2
125000004093 cyano group Chemical group *C#N 0.000 claims 2
125000000753 cycloalkyl group Chemical group 0.000 claims 2
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims 2
XLZQTIOJCSNQPD-UHFFFAOYSA-N (n-ethylanilino) hydrogen sulfate Chemical compound OS(=O)(=O)ON(CC)C1=CC=CC=C1 XLZQTIOJCSNQPD-UHFFFAOYSA-N 0.000 claims 1
125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 claims 1
JUDMNPJWHXETRI-UHFFFAOYSA-N 1,2-dimethylpyrazole Chemical compound CN1[CH][CH][CH]N1C JUDMNPJWHXETRI-UHFFFAOYSA-N 0.000 claims 1
OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 claims 1
VFJPKSBMVGVBQR-UHFFFAOYSA-N 1-methyl-3-[3-(trifluoromethyl)phenyl]pyrazole Chemical compound CN1C=CC(C=2C=C(C=CC=2)C(F)(F)F)=N1 VFJPKSBMVGVBQR-UHFFFAOYSA-N 0.000 claims 1
MQSBVYINPUYVMT-UHFFFAOYSA-N 1-tert-butyl-3-methylpyrazole Chemical compound CC=1C=CN(C(C)(C)C)N=1 MQSBVYINPUYVMT-UHFFFAOYSA-N 0.000 claims 1
ZVAPWJGRRUHKGP-UHFFFAOYSA-N 1h-1,5-benzodiazepine Chemical compound N1C=CC=NC2=CC=CC=C12 ZVAPWJGRRUHKGP-UHFFFAOYSA-N 0.000 claims 1
POYXMTCMZAMQAW-UHFFFAOYSA-N 2,4-dimethyl-1h-pyrazol-5-one Chemical compound CC1=CN(C)N=C1O POYXMTCMZAMQAW-UHFFFAOYSA-N 0.000 claims 1
OAFMLNIISNFEIP-UHFFFAOYSA-N 2-(3-methylpyrazol-1-yl)ethanol Chemical compound CC=1C=CN(CCO)N=1 OAFMLNIISNFEIP-UHFFFAOYSA-N 0.000 claims 1
RKXRIMKWGHBIIN-UHFFFAOYSA-N 2-(3-phenylpyrazol-1-yl)pyridine Chemical compound C1=CN(C=2N=CC=CC=2)N=C1C1=CC=CC=C1 RKXRIMKWGHBIIN-UHFFFAOYSA-N 0.000 claims 1
IMRWILPUOVGIMU-UHFFFAOYSA-N 2-bromopyridine Chemical compound BrC1=CC=CC=N1 IMRWILPUOVGIMU-UHFFFAOYSA-N 0.000 claims 1
LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical group CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 claims 1
BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 claims 1
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
BRJXEBWSMSDYSQ-UHFFFAOYSA-N 3-(1-methylpyrazol-3-yl)pyridine Chemical compound CN1C=CC(C=2C=NC=CC=2)=N1 BRJXEBWSMSDYSQ-UHFFFAOYSA-N 0.000 claims 1
FGAQOSUKYVXCIE-UHFFFAOYSA-N 3-(2-methoxyethoxymethyl)-1-methylpyrazole Chemical compound COCCOCC=1C=CN(C)N=1 FGAQOSUKYVXCIE-UHFFFAOYSA-N 0.000 claims 1
JTPDYCJCXHROHL-UHFFFAOYSA-N 3-cyclohexyl-1-methylpyrazole Chemical compound CN1C=CC(C2CCCCC2)=N1 JTPDYCJCXHROHL-UHFFFAOYSA-N 0.000 claims 1
DIBFBUQGVMZWTM-UHFFFAOYSA-N 4-(trifluoromethyl)-2h-triazole Chemical group FC(F)(F)C=1C=NNN=1 DIBFBUQGVMZWTM-UHFFFAOYSA-N 0.000 claims 1
125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims 1
SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 claims 1
GVSNQMFKEPBIOY-UHFFFAOYSA-N 4-methyl-2h-triazole Chemical group CC=1C=NNN=1 GVSNQMFKEPBIOY-UHFFFAOYSA-N 0.000 claims 1
RISQWZNRZAZRPJ-UHFFFAOYSA-N 5-cyclohexyl-1h-pyrazole Chemical compound C1CCCCC1C1=NNC=C1 RISQWZNRZAZRPJ-UHFFFAOYSA-N 0.000 claims 1
QRQGYUIBFTVPIB-UHFFFAOYSA-N C[S+](C=C1)C=C1C1=NNC=C1 Chemical compound C[S+](C=C1)C=C1C1=NNC=C1 QRQGYUIBFTVPIB-UHFFFAOYSA-N 0.000 claims 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
CVLAEJNQNKXNNN-UHFFFAOYSA-N diazepin-4-one Chemical compound O=C1C=CC=NN=C1 CVLAEJNQNKXNNN-UHFFFAOYSA-N 0.000 claims 1
229940117389 dichlorobenzene Drugs 0.000 claims 1
FQYYIPZPELSLDK-UHFFFAOYSA-N ethyl pyridine-2-carboxylate Chemical compound CCOC(=O)C1=CC=CC=N1 FQYYIPZPELSLDK-UHFFFAOYSA-N 0.000 claims 1
229910052736 halogen Inorganic materials 0.000 claims 1
125000005059 halophenyl group Chemical group 0.000 claims 1
125000001841 imino group Chemical group [H]N=* 0.000 claims 1
NEPZGUGQLAOODR-UHFFFAOYSA-N methyl 5-methylthiophene-2-carboxylate Chemical compound COC(=O)C1=CC=C(C)S1 NEPZGUGQLAOODR-UHFFFAOYSA-N 0.000 claims 1
XLSZMDLNRCVEIJ-UHFFFAOYSA-N methylimidazole Chemical group CC1=CNC=N1 XLSZMDLNRCVEIJ-UHFFFAOYSA-N 0.000 claims 1
PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 claims 1
FWUVIDBCGSLNND-UHFFFAOYSA-N morpholin-4-yl(pyridin-2-yl)methanone Chemical compound C=1C=CC=NC=1C(=O)N1CCOCC1 FWUVIDBCGSLNND-UHFFFAOYSA-N 0.000 claims 1
RURVGUVIDIBFBF-UHFFFAOYSA-N n-(1-ethoxyethyl)cyclohexa-2,4-dien-1-imine Chemical compound CCOC(C)N=C1CC=CC=C1 RURVGUVIDIBFBF-UHFFFAOYSA-N 0.000 claims 1
IDSCGIREUASONG-UHFFFAOYSA-N n-tert-butylpyridine-2-carboxamide Chemical compound CC(C)(C)NC(=O)C1=CC=CC=N1 IDSCGIREUASONG-UHFFFAOYSA-N 0.000 claims 1
125000003431 oxalo group Chemical group 0.000 claims 1
UDJFFSGCRRMVFH-UHFFFAOYSA-N pyrido[2,3-d]pyrimidine Chemical compound N1=CN=CC2=CC=CN=C21 UDJFFSGCRRMVFH-UHFFFAOYSA-N 0.000 claims 1
VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical group OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 claims 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
150000003536 tetrazoles Chemical group 0.000 claims 1
125000004496 thiazol-5-yl group Chemical group S1C=NC=C1* 0.000 claims 1
FFSJPOPLSWBGQY-UHFFFAOYSA-N triazol-4-one Chemical group O=C1C=NN=N1 FFSJPOPLSWBGQY-UHFFFAOYSA-N 0.000 claims 1
150000003852 triazoles Chemical group 0.000 claims 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract description 30
230000002776 aggregation Effects 0.000 abstract description 2
239000005557 antagonist Substances 0.000 abstract description 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 2
125000002373 5 membered heterocyclic group Chemical group 0.000 abstract 1
238000005054 agglomeration Methods 0.000 abstract 1
150000001555 benzenes Chemical class 0.000 abstract 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 1
239000000203 mixture Substances 0.000 description 81
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 78
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 67
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 57
238000000034 method Methods 0.000 description 54
239000000243 solution Substances 0.000 description 49
238000002360 preparation method Methods 0.000 description 48
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 45
239000007787 solid Substances 0.000 description 44
239000002904 solvent Substances 0.000 description 43
239000000047 product Substances 0.000 description 40
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
238000010992 reflux Methods 0.000 description 30
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 29
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 25
238000004458 analytical method Methods 0.000 description 24
238000003818 flash chromatography Methods 0.000 description 24
UKWHYYKOEPRTIC-UHFFFAOYSA-N mercury(ii) oxide Chemical compound [Hg]=O UKWHYYKOEPRTIC-UHFFFAOYSA-N 0.000 description 22
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 19
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 16
239000002253 acid Substances 0.000 description 16
229920006395 saturated elastomer Polymers 0.000 description 16
239000000284 extract Substances 0.000 description 15
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 14
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 14
239000012312 sodium hydride Substances 0.000 description 14
229910000104 sodium hydride Inorganic materials 0.000 description 14
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 13
239000000725 suspension Substances 0.000 description 13
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
239000011541 reaction mixture Substances 0.000 description 12
239000011734 sodium Substances 0.000 description 12
229910052708 sodium Inorganic materials 0.000 description 12
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 description 11
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
239000000706 filtrate Substances 0.000 description 11
229940101209 mercuric oxide Drugs 0.000 description 11
239000000377 silicon dioxide Substances 0.000 description 11
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 11
239000000543 intermediate Substances 0.000 description 10
239000012044 organic layer Substances 0.000 description 10
238000001953 recrystallisation Methods 0.000 description 9
229960000583 acetic acid Drugs 0.000 description 8
238000006243 chemical reaction Methods 0.000 description 8
239000012043 crude product Substances 0.000 description 8
239000006185 dispersion Substances 0.000 description 8
AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical compound CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 description 8
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 8
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 8
229910052943 magnesium sulfate Inorganic materials 0.000 description 7
235000019341 magnesium sulphate Nutrition 0.000 description 7
235000017557 sodium bicarbonate Nutrition 0.000 description 7
229910000030 sodium bicarbonate Inorganic materials 0.000 description 7
238000012360 testing method Methods 0.000 description 7
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 6
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
230000000172 allergic effect Effects 0.000 description 6
208000010668 atopic eczema Diseases 0.000 description 6
230000015572 biosynthetic process Effects 0.000 description 6
235000010288 sodium nitrite Nutrition 0.000 description 6
238000005059 solid analysis Methods 0.000 description 6
238000003756 stirring Methods 0.000 description 6
239000001117 sulphuric acid Substances 0.000 description 6
235000011149 sulphuric acid Nutrition 0.000 description 6
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
150000001412 amines Chemical group 0.000 description 5
239000003054 catalyst Substances 0.000 description 5
238000001914 filtration Methods 0.000 description 5
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 5
239000000463 material Substances 0.000 description 5
239000012074 organic phase Substances 0.000 description 5
238000000746 purification Methods 0.000 description 5
239000000741 silica gel Substances 0.000 description 5
229910002027 silica gel Inorganic materials 0.000 description 5
238000003786 synthesis reaction Methods 0.000 description 5
238000011282 treatment Methods 0.000 description 5
SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 4
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 4
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ONTQJDKFANPPKK-UHFFFAOYSA-L chembl3185981 Chemical compound [Na+].[Na+].CC1=CC(C)=C(S([O-])(=O)=O)C=C1N=NC1=CC(S([O-])(=O)=O)=C(C=CC=C2)C2=C1O ONTQJDKFANPPKK-UHFFFAOYSA-L 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
230000001684 chronic effect Effects 0.000 description 1
238000004040 coloring Methods 0.000 description 1
229940125758 compound 15 Drugs 0.000 description 1
238000009109 curative therapy Methods 0.000 description 1
239000012024 dehydrating agents‎ Substances 0.000 description 1
230000005595 deprotonation Effects 0.000 description 1
238000010537 deprotonation reaction Methods 0.000 description 1
125000002576 diazepinyl group Chemical class N1N=C(C=CC=C1)* 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
229960001760 dimethyl sulfoxide Drugs 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
230000002526 effect on cardiovascular system Effects 0.000 description 1
239000002158 endotoxin Substances 0.000 description 1
230000003628 erosive effect Effects 0.000 description 1
IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
FCZCIXQGZOUIDN-UHFFFAOYSA-N ethyl 2-diethoxyphosphinothioyloxyacetate Chemical compound CCOC(=O)COP(=S)(OCC)OCC FCZCIXQGZOUIDN-UHFFFAOYSA-N 0.000 description 1
239000002038 ethyl acetate fraction Substances 0.000 description 1
UKFXDFUAPNAMPJ-UHFFFAOYSA-N ethylmalonic acid Chemical compound CCC(C(O)=O)C(O)=O UKFXDFUAPNAMPJ-UHFFFAOYSA-N 0.000 description 1
230000007717 exclusion Effects 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
210000001156 gastric mucosa Anatomy 0.000 description 1
238000003304 gavage Methods 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
230000002008 hemorrhagic effect Effects 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
150000002460 imidazoles Chemical class 0.000 description 1
150000002462 imidazolines Chemical group 0.000 description 1
125000002636 imidazolinyl group Chemical group 0.000 description 1
210000004969 inflammatory cell Anatomy 0.000 description 1
YOBAEOGBNPPUQV-UHFFFAOYSA-N iron;trihydrate Chemical compound O.O.O.[Fe].[Fe] YOBAEOGBNPPUQV-UHFFFAOYSA-N 0.000 description 1
208000028867 ischemia Diseases 0.000 description 1
125000000468 ketone group Chemical group 0.000 description 1
230000001665 lethal effect Effects 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
210000003975 mesenteric artery Anatomy 0.000 description 1
239000002032 methanolic fraction Substances 0.000 description 1
IMAKHNTVDGLIRY-UHFFFAOYSA-N methyl prop-2-ynoate Chemical compound COC(=O)C#C IMAKHNTVDGLIRY-UHFFFAOYSA-N 0.000 description 1
JYXPWUYLZPYOAH-UHFFFAOYSA-N methylhydrazine Chemical compound CN=N JYXPWUYLZPYOAH-UHFFFAOYSA-N 0.000 description 1
XONPDZSGENTBNJ-UHFFFAOYSA-N molecular hydrogen;sodium Chemical compound [Na].[H][H] XONPDZSGENTBNJ-UHFFFAOYSA-N 0.000 description 1
239000002808 molecular sieve Substances 0.000 description 1
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 description 1
210000000440 neutrophil Anatomy 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
JQPTYAILLJKUCY-UHFFFAOYSA-N palladium(ii) oxide Chemical class [O-2].[Pd+2] JQPTYAILLJKUCY-UHFFFAOYSA-N 0.000 description 1
NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
230000001991 pathophysiological effect Effects 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
239000012071 phase Substances 0.000 description 1
125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000011698 potassium fluoride Substances 0.000 description 1
235000003270 potassium fluoride Nutrition 0.000 description 1
230000002062 proliferating effect Effects 0.000 description 1
238000011321 prophylaxis Methods 0.000 description 1
230000001185 psoriatic effect Effects 0.000 description 1
208000002815 pulmonary hypertension Diseases 0.000 description 1
XYEVREOOMFVLLS-UHFFFAOYSA-N pyrazolo[4,3-c]diazepine Chemical class C1=CC=NN=C2C=NN=C21 XYEVREOOMFVLLS-UHFFFAOYSA-N 0.000 description 1
125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
230000002441 reversible effect Effects 0.000 description 1
238000006798 ring closing metathesis reaction Methods 0.000 description 1
229910001494 silver tetrafluoroborate Inorganic materials 0.000 description 1
150000003385 sodium Chemical class 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
239000011343 solid material Substances 0.000 description 1
239000012265 solid product Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
239000001119 stannous chloride Substances 0.000 description 1
235000011150 stannous chloride Nutrition 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
230000009885 systemic effect Effects 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
RZWIIPASKMUIAC-VQTJNVASSA-N thromboxane Chemical compound CCCCCCCC[C@H]1OCCC[C@@H]1CCCCCCC RZWIIPASKMUIAC-VQTJNVASSA-N 0.000 description 1
DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical compound CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 0.000 description 1
JFALSRSLKYAFGM-UHFFFAOYSA-N uranium(0) Chemical compound [U] JFALSRSLKYAFGM-UHFFFAOYSA-N 0.000 description 1

Classifications

- 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
- C07D401/10—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 carbon chain containing aromatic rings
- 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
- A61P37/08—Antiallergic agents
- 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
- C07D403/10—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 carbon chain containing aromatic 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Public Health (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Pulmonology (AREA)
Immunology (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Pain & Pain Management (AREA)
Rheumatology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Plural Heterocyclic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

IL9377690A 1989-03-23 1990-03-16 Antilateral substances of type 1,4 - pretty, fresh and molten tetracyclic diazepines and pharmaceutical preparations containing them IL93776A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB898906813A GB8906813D0 (en)	1989-03-23	1989-03-23	Therapeutic agents
GB898926246A GB8926246D0 (en)	1989-11-21	1989-11-21	Therapeutic agents

Publications (2)

Publication Number	Publication Date
IL93776A0 IL93776A0 (en)	1990-12-23
IL93776A true IL93776A (en)	1994-10-21

Family

ID=26295132

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL9377690A IL93776A (en)	1989-03-23	1990-03-16	Antilateral substances of type 1,4 - pretty, fresh and molten tetracyclic diazepines and pharmaceutical preparations containing them

Country Status (21)

Country	Link
US (1)	US5008263A (de)
EP (1)	EP0389189B1 (de)
JP (1)	JPH0684371B2 (de)
KR (1)	KR920003981B1 (de)
CN (1)	CN1045783A (de)
AT (1)	ATE105839T1 (de)
AU (1)	AU627286B2 (de)
CA (1)	CA2012666C (de)
DE (1)	DE69008906T2 (de)
DK (1)	DK0389189T3 (de)
ES (1)	ES2052172T3 (de)
FI (1)	FI98463C (de)
HU (1)	HUT61006A (de)
IE (1)	IE62857B1 (de)
IL (1)	IL93776A (de)
MY (1)	MY106322A (de)
NO (1)	NO175151C (de)
NZ (1)	NZ233047A (de)
PH (1)	PH27513A (de)
PT (1)	PT93526B (de)
YU (1)	YU47344B (de)

Families Citing this family (23)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB9010404D0 (en) *	1990-05-09	1990-06-27	Pfizer Ltd	Therapeutic agents
GB9015524D0 (en) *	1990-07-13	1990-08-29	Pfizer Ltd	Therapeutic agents
GB9019409D0 (en) *	1990-09-05	1990-10-17	Pfizer Ltd	Therapeutic agents
GB9019833D0 (en) *	1990-09-11	1990-10-24	Pfizer Ltd	Therapeutic agents
WO1993000095A2 (en) *	1991-06-28	1993-01-07	Smithkline Beecham Corporation	Bicyclic fibrinogen antagonists
US5939412A (en) *	1992-06-26	1999-08-17	Smithkline Beecham Corporation	Bicyclic fibrinogen antagonists
IL108524A0 (en) *	1993-02-03	1994-05-30	Gensia Inc	Imidazodiazepine analogs
US5500439A (en) *	1993-12-09	1996-03-19	Alteon Inc.	Aminopyrazoles
MA23420A1 (fr) *	1994-01-07	1995-10-01	Smithkline Beecham Corp	Antagonistes bicycliques de fibrinogene.
JPH10500402A (ja) *	1994-04-29	1998-01-13	武田薬品工業株式会社	縮合複素環化合物またはその塩、その製造法および用途
US6458784B1 (en)	1994-06-29	2002-10-01	Smithkline Beecham Corporation	Vitronectin receptor antagonists
FR2733749B1 (fr)	1995-05-05	1997-06-13	Oreal	Compositions pour la teinture des fibres keratiniques contenant des diamino pyrazoles, procede de teinture, nouveaux diamino pyrazoles et leur procede de preparation
US5726171A (en) *	1995-06-07	1998-03-10	Merck & Co Inc	N-(1-alkyl-5-phenyl-2,3,4,5-tetrahydro-1H-benzo B! 1,4!diazepin-3yl)-acetamides
US5977101A (en) *	1995-06-29	1999-11-02	Smithkline Beecham Corporation	Benzimidazoles/Imidazoles Linked to a Fibrinogen Receptor Antagonist Template Having Vitronectin Receptor Antagonist Activity
ES2294789T3 (es) *	1995-08-15	2008-04-01	Bayer Cropscience Ag	Derivados de indazol pesticidas.
US6172222B1 (en)	1998-06-08	2001-01-09	American Home Products Corporation	Diaminopyrazoles
US6458823B1 (en)	1998-06-08	2002-10-01	Wyeth	Diaminopyrazoles
US6949542B2 (en) *	2002-02-06	2005-09-27	Hoffman-La Roche Inc.	Dihydro-benzo[b][1,4]diazepin-2-one derivatives
US8546377B2 (en)	2009-04-23	2013-10-01	Abbvie Inc.	Modulators of 5-HT receptors and methods of use thereof
US8518933B2 (en)	2009-04-23	2013-08-27	Abbvie Inc.	Modulators of 5-HT receptors and methods of use thereof
WO2012061342A2 (en)	2010-11-01	2012-05-10	Arqule, Inc.	Substituted benzo-imidazo-pyrido-diazepine compounds
KR101675984B1 (ko)	2015-02-23	2016-11-14	한양대학교 에리카산학협력단	티에노디아제핀 유도체 또는 이의 약학적으로 허용가능한 염, 및 이를 유효성분으로 포함하는 약학적 조성물
CN105153195B (zh) *	2015-09-01	2017-09-26	汤文建	一种三环吡唑[1,5‑d][1,4]苯并氧氮杂卓酮衍生物及其制备方法与用途

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AU527689B2 (en) *	1974-09-11	1983-03-17	F. Hoffmann-La Roche & Co.	Imidazodiazepine derivatives
DK476885D0 (da) *	1985-10-17	1985-10-17	Ferrosan As	Heterocycliske forbindelser og fremgangsmaader til fremstilling heraf
DE3778559D1 (de) *	1986-01-21	1992-06-04	Boehringer Ingelheim Kg	Thieno-1,4-diazepine.

1990
- 1990-03-15 AT AT90302826T patent/ATE105839T1/de not_active IP Right Cessation
- 1990-03-15 EP EP90302826A patent/EP0389189B1/de not_active Expired - Lifetime
- 1990-03-15 DE DE69008906T patent/DE69008906T2/de not_active Expired - Fee Related
- 1990-03-15 DK DK90302826.4T patent/DK0389189T3/da active
- 1990-03-15 ES ES90302826T patent/ES2052172T3/es not_active Expired - Lifetime
- 1990-03-16 IL IL9377690A patent/IL93776A/en not_active IP Right Cessation
- 1990-03-20 US US07/496,393 patent/US5008263A/en not_active Expired - Fee Related
- 1990-03-21 MY MYPI90000443A patent/MY106322A/en unknown
- 1990-03-21 PT PT93526A patent/PT93526B/pt not_active IP Right Cessation
- 1990-03-21 CA CA002012666A patent/CA2012666C/en not_active Expired - Fee Related
- 1990-03-22 PH PH40251A patent/PH27513A/en unknown
- 1990-03-22 FI FI901441A patent/FI98463C/fi not_active IP Right Cessation
- 1990-03-22 IE IE105590A patent/IE62857B1/en not_active IP Right Cessation
- 1990-03-22 KR KR1019900003870A patent/KR920003981B1/ko not_active Expired
- 1990-03-22 NO NO901329A patent/NO175151C/no unknown
- 1990-03-22 YU YU56390A patent/YU47344B/sh unknown
- 1990-03-22 NZ NZ233047A patent/NZ233047A/en unknown
- 1990-03-22 HU HU901794A patent/HUT61006A/hu unknown
- 1990-03-22 AU AU52148/90A patent/AU627286B2/en not_active Ceased
- 1990-03-23 CN CN90101559A patent/CN1045783A/zh not_active Withdrawn
- 1990-03-23 JP JP2075339A patent/JPH0684371B2/ja not_active Expired - Lifetime

Also Published As

Publication number	Publication date
FI98463C (fi)	1997-06-25
DE69008906T2 (de)	1994-08-25
KR900014387A (ko)	1990-10-23
DK0389189T3 (da)	1994-06-20
CN1045783A (zh)	1990-10-03
ES2052172T3 (es)	1994-07-01
HUT61006A (en)	1992-11-30
YU56390A (sh)	1992-12-21
NO175151C (no)	1994-09-07
DE69008906D1 (de)	1994-06-23
NO175151B (no)	1994-05-30
IE62857B1 (en)	1995-03-08
MY106322A (en)	1995-05-30
YU47344B (sh)	1995-01-31
FI901441A0 (fi)	1990-03-22
CA2012666C (en)	1997-01-28
EP0389189A2 (de)	1990-09-26
CA2012666A1 (en)	1990-09-23
PH27513A (en)	1993-08-18
IL93776A0 (en)	1990-12-23
NO901329D0 (no)	1990-03-22
KR920003981B1 (ko)	1992-05-21
US5008263A (en)	1991-04-16
AU5214890A (en)	1990-11-01
IE901055L (en)	1990-09-23
JPH0314577A (ja)	1991-01-23
HU901794D0 (en)	1990-06-28
ATE105839T1 (de)	1994-06-15
AU627286B2 (en)	1992-08-20
FI98463B (fi)	1997-03-14
PT93526B (pt)	1996-08-30
PT93526A (pt)	1990-11-07
NZ233047A (en)	1992-06-25
JPH0684371B2 (ja)	1994-10-26
EP0389189B1 (de)	1994-05-18
NO901329L (no)	1990-09-24
EP0389189A3 (de)	1991-08-21

Legal Events

Date	Code	Title	Description
1996-12-05	RH	Patent void

Publication	Publication Date	Title
IL93776A (en)	1994-10-21	Antilateral substances of type 1,4 - pretty, fresh and molten tetracyclic diazepines and pharmaceutical preparations containing them
US5250531A (en)	1993-10-05	Dihydropyrimidine antiallergy agents
JP2001512125A (ja)	2001-08-21	三環系バソプレシンアゴニスト
US5248681A (en)	1993-09-28	Dihydropyridine antiallergy agents
US4894377A (en)	1990-01-16	β-carbolines and their use as medicinal agents
JPH0565288A (ja)	1993-03-19	新規なアシルアミノ置換ヘトラゼピン誘導体、その製法及びそれを含有する医薬組成物
EP0294074B1 (de)	1992-04-08	Dihydropyridine mit antiallergischer und antiinflammatorischer Wirkung
EP0330327A2 (de)	1989-08-30	Dihydropyridine, ihre Herstellung und ihre Verwendung als PAF-Antagonisten
HU197011B (en)	1989-02-28	Process for producing new imidazo- and triazolo-1,4-benzodiazepines and pharmaceuticals comprising the same
JPH04261181A (ja)	1992-09-17	新規なヘトラゼピノイドアミド
JP2001512120A (ja)	2001-08-21	三環系バソプレシンアゴニスト
JPH08503944A (ja)	1996-04-30	ＰＡＦアンタゴニストとしての置換−フェニル（Ｎ，Ｎ’−シクロアルキル／アルキルカルボキシアミド）−１Ｈ／３Ｈ−イミダゾ〔４，５−ｂ〕ピリジン化合物
WO1992004349A1 (en)	1992-03-19	Therapeutic agents
EP0462986B1 (de)	1993-10-06	Imidazopyrimidine, antiallergische heilmittel
US5214044A (en)	1993-05-25	1,4-dihydropyridines useful as pharmaceuticals
IE913102A1 (en)	1992-03-11	Therapeutic agents
DD292914A5 (de)	1991-08-14	Verfahren zur herstellung von diazepin-derivaten
MXPA00000749A (en)	2001-11-21	Tricyclic vasopressin agonists
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