CA1057286A - Pyridobenzodiazepinones, procede pour leur preparation et produits pharmaceutiques en contenant - Google Patents

Pyridobenzodiazepinones, procede pour leur preparation et produits pharmaceutiques en contenant

Info

Publication number: CA1057286A
Authority: CA; Canada
Prior art keywords: methyl; pyrido; dihydro; benzodiazepin; process according
Prior art date: 1974-02-20
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA227,479A

Other languages

English (en)

Other versions

CA227479S (en

Inventor

Gunther Engelhardt

Gunther Schmidt

Sigfrid Puschmann

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Boehringer Ingelheim Pharma GmbH and Co KG

Original Assignee

Dr Karl Thomae GmbH

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.)

1974-02-20

Filing date

1975-05-21

Publication date

1979-06-26

1974-02-20 Priority claimed from DE19742408111 external-priority patent/DE2408111C3/de

1975-05-21 Application filed by Dr Karl Thomae GmbH filed Critical Dr Karl Thomae GmbH

1979-06-26 Application granted granted Critical

1979-06-26 Publication of CA1057286A publication Critical patent/CA1057286A/fr

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 152
230000008569 process Effects 0.000 title claims abstract description 143
150000001875 compounds Chemical class 0.000 title claims abstract description 51
MGDDXKBVXQCWER-UHFFFAOYSA-N pyrido[2,3-i][1,2]benzodiazepin-3-one Chemical class N1=NC(=O)C=CC2=CC=C(N=CC=C3)C3=C21 MGDDXKBVXQCWER-UHFFFAOYSA-N 0.000 title claims abstract description 5
238000002360 preparation method Methods 0.000 title abstract description 5
239000003814 drug Substances 0.000 title 1
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 45
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 45
229910052757 nitrogen Inorganic materials 0.000 claims description 44
-1 pyrrolidino, piperidino Chemical group 0.000 claims description 44
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 40
239000012312 sodium hydride Substances 0.000 claims description 40
229910000104 sodium hydride Inorganic materials 0.000 claims description 40
239000000126 substance Substances 0.000 claims description 36
238000006243 chemical reaction Methods 0.000 claims description 35
ONUDKSCEPDVUPP-UHFFFAOYSA-N 6-methyl-11h-pyrido[3,2-c][1,5]benzodiazepin-5-one Chemical compound O=C1N(C)C2=CC=CC=C2NC2=NC=CC=C21 ONUDKSCEPDVUPP-UHFFFAOYSA-N 0.000 claims description 23
238000011065 in-situ storage Methods 0.000 claims description 22
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 21
125000004433 nitrogen atom Chemical group N* 0.000 claims description 17
ZGLDQGIONSGJCN-UHFFFAOYSA-N diazepin-5-one Chemical compound O=C1C=CN=NC=C1 ZGLDQGIONSGJCN-UHFFFAOYSA-N 0.000 claims description 16
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
239000002253 acid Substances 0.000 claims description 14
HCDXLUKTYFLIEM-UHFFFAOYSA-N 1,2-benzodiazepin-5-one Chemical compound O=C1C=CN=NC2=CC=CC=C12 HCDXLUKTYFLIEM-UHFFFAOYSA-N 0.000 claims description 9
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 9
150000003839 salts Chemical class 0.000 claims description 9
229910052739 hydrogen Inorganic materials 0.000 claims description 8
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 8
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 7
125000000217 alkyl group Chemical group 0.000 claims description 7
239000001257 hydrogen Substances 0.000 claims description 7
239000012442 inert solvent Substances 0.000 claims description 7
229910052708 sodium Inorganic materials 0.000 claims description 7
239000011734 sodium Substances 0.000 claims description 7
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 7
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
125000004432 carbon atom Chemical group C* 0.000 claims description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
WVUULNDRFBHTFG-UHFFFAOYSA-N 3-chloro-n,n-diethylpropan-1-amine Chemical compound CCN(CC)CCCCl WVUULNDRFBHTFG-UHFFFAOYSA-N 0.000 claims description 5
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims description 5
238000010438 heat treatment Methods 0.000 claims description 4
DBVADBHSJCWFKI-UHFFFAOYSA-N n-(2-chloroethyl)-n-propan-2-ylpropan-2-amine Chemical compound CC(C)N(C(C)C)CCCl DBVADBHSJCWFKI-UHFFFAOYSA-N 0.000 claims description 4
HDDNBUNZJIQDBQ-UHFFFAOYSA-N 1-(3-chloropropyl)piperidine Chemical compound ClCCCN1CCCCC1 HDDNBUNZJIQDBQ-UHFFFAOYSA-N 0.000 claims description 3
SPRTXTPFQKHSBG-UHFFFAOYSA-N 1-(3-chloropropyl)pyrrolidine Chemical compound ClCCCN1CCCC1 SPRTXTPFQKHSBG-UHFFFAOYSA-N 0.000 claims description 3
YMDNODNLFSHHCV-UHFFFAOYSA-N 2-chloro-n,n-diethylethanamine Chemical compound CCN(CC)CCCl YMDNODNLFSHHCV-UHFFFAOYSA-N 0.000 claims description 3
WQMAANNAZKNUDL-UHFFFAOYSA-N 2-dimethylaminoethyl chloride Chemical compound CN(C)CCCl WQMAANNAZKNUDL-UHFFFAOYSA-N 0.000 claims description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 3
229910052783 alkali metal Inorganic materials 0.000 claims description 3
125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 claims description 3
RMGFLMXDCGQKPS-UHFFFAOYSA-N 1-(2-chloroethyl)pyrrolidine Chemical compound ClCCN1CCCC1 RMGFLMXDCGQKPS-UHFFFAOYSA-N 0.000 claims description 2
HBOZHTSTTRVJNT-UHFFFAOYSA-N 1-(3-chloropropyl)azepane Chemical compound ClCCCN1CCCCCC1 HBOZHTSTTRVJNT-UHFFFAOYSA-N 0.000 claims description 2
RXYQHVMJQFHKDX-UHFFFAOYSA-N 3-chloro-n,n-di(propan-2-yl)propan-1-amine Chemical compound CC(C)N(C(C)C)CCCCl RXYQHVMJQFHKDX-UHFFFAOYSA-N 0.000 claims description 2
NYYRRBOMNHUCLB-UHFFFAOYSA-N 3-chloro-n,n-dimethylpropan-1-amine Chemical compound CN(C)CCCCl NYYRRBOMNHUCLB-UHFFFAOYSA-N 0.000 claims description 2
FKXYUGSJUMXROI-UHFFFAOYSA-N 3-chloro-n,n-dipropylpropan-1-amine Chemical compound CCCN(CCC)CCCCl FKXYUGSJUMXROI-UHFFFAOYSA-N 0.000 claims description 2
150000001340 alkali metals Chemical group 0.000 claims description 2
SIAPCJWMELPYOE-UHFFFAOYSA-N lithium hydride Chemical compound [LiH] SIAPCJWMELPYOE-UHFFFAOYSA-N 0.000 claims description 2
229910000103 lithium hydride Inorganic materials 0.000 claims description 2
GTNGRRLCBNNJHB-UHFFFAOYSA-N n-benzyl-3-chloro-n-ethylpropan-1-amine Chemical compound ClCCCN(CC)CC1=CC=CC=C1 GTNGRRLCBNNJHB-UHFFFAOYSA-N 0.000 claims description 2
NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 claims description 2
229910000105 potassium hydride Inorganic materials 0.000 claims description 2
BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 claims description 2
159000000000 sodium salts Chemical class 0.000 claims 38
SVUFORYXDVGXLZ-UHFFFAOYSA-N 5-methyl-11h-pyrido[2,3-b][1,4]benzodiazepin-6-one Chemical compound O=C1N(C)C2=CC=CN=C2NC2=CC=CC=C21 SVUFORYXDVGXLZ-UHFFFAOYSA-N 0.000 claims 16
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 12
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 claims 12
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 9
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 7
WFSHZGWLACIEOH-UHFFFAOYSA-N 11-[3-(diethylamino)propyl]-6-methylpyrido[3,2-c][1,5]benzodiazepin-5-one Chemical compound CN1C(=O)C2=CC=CN=C2N(CCCN(CC)CC)C2=CC=CC=C21 WFSHZGWLACIEOH-UHFFFAOYSA-N 0.000 claims 5
YVWTUJZOCOEVAY-UHFFFAOYSA-N 11-[3-(dimethylamino)propyl]-5-methylpyrido[2,3-b][1,4]benzodiazepin-6-one Chemical compound O=C1N(C)C2=CC=CN=C2N(CCCN(C)C)C2=CC=CC=C21 YVWTUJZOCOEVAY-UHFFFAOYSA-N 0.000 claims 5
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims 5
238000007327 hydrogenolysis reaction Methods 0.000 claims 5
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims 4
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 4
ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical group C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 claims 4
229940043279 diisopropylamine Drugs 0.000 claims 4
DSOMRPCJWSFSTC-UHFFFAOYSA-N 11-[2-(diethylamino)ethyl]-5-methylpyrido[2,3-b][1,4]benzodiazepin-6-one Chemical compound O=C1N(C)C2=CC=CN=C2N(CCN(CC)CC)C2=CC=CC=C21 DSOMRPCJWSFSTC-UHFFFAOYSA-N 0.000 claims 3
RWBYWHWENFEGSZ-UHFFFAOYSA-N 11-[2-[di(propan-2-yl)amino]ethyl]-5-methylpyrido[2,3-b][1,4]benzodiazepin-6-one Chemical compound O=C1N(C)C2=CC=CN=C2N(CCN(C(C)C)C(C)C)C2=CC=CC=C21 RWBYWHWENFEGSZ-UHFFFAOYSA-N 0.000 claims 3
KIEZOEAFTBLRGY-UHFFFAOYSA-N 11-[3-(azepan-1-yl)propyl]-5-methylpyrido[2,3-b][1,4]benzodiazepin-6-one Chemical compound C12=CC=CC=C2C(=O)N(C)C2=CC=CN=C2N1CCCN1CCCCCC1 KIEZOEAFTBLRGY-UHFFFAOYSA-N 0.000 claims 3
XYCOIJWGYALTDE-UHFFFAOYSA-N 11-[3-(azepan-1-yl)propyl]-6-methylpyrido[3,2-c][1,5]benzodiazepin-5-one Chemical compound C12=NC=CC=C2C(=O)N(C)C2=CC=CC=C2N1CCCN1CCCCCC1 XYCOIJWGYALTDE-UHFFFAOYSA-N 0.000 claims 3
AOQYIDLKEFDVHW-UHFFFAOYSA-N 11-[3-(diethylamino)propyl]-5-methylpyrido[2,3-b][1,4]benzodiazepin-6-one Chemical compound O=C1N(C)C2=CC=CN=C2N(CCCN(CC)CC)C2=CC=CC=C21 AOQYIDLKEFDVHW-UHFFFAOYSA-N 0.000 claims 3
YTMYYNLTGLBQIR-UHFFFAOYSA-N 11-[3-(ethylamino)propyl]-6-methylpyrido[3,2-c][1,5]benzodiazepin-5-one Chemical compound CN1C(=O)C2=CC=CN=C2N(CCCNCC)C2=CC=CC=C21 YTMYYNLTGLBQIR-UHFFFAOYSA-N 0.000 claims 3
XVPFIBARQISXDS-UHFFFAOYSA-N 11-[3-[di(propan-2-yl)amino]propyl]-5-methylpyrido[2,3-b][1,4]benzodiazepin-6-one Chemical compound O=C1N(C)C2=CC=CN=C2N(CCCN(C(C)C)C(C)C)C2=CC=CC=C21 XVPFIBARQISXDS-UHFFFAOYSA-N 0.000 claims 3
NIAXLCRQKUVKKE-UHFFFAOYSA-N 5-methyl-11-(3-piperidin-1-ylpropyl)pyrido[2,3-b][1,4]benzodiazepin-6-one Chemical compound C12=CC=CC=C2C(=O)N(C)C2=CC=CN=C2N1CCCN1CCCCC1 NIAXLCRQKUVKKE-UHFFFAOYSA-N 0.000 claims 3
SKQUVSXNFDZXJA-UHFFFAOYSA-N 5-methyl-11-(3-pyrrolidin-1-ylpropyl)pyrido[2,3-b][1,4]benzodiazepin-6-one Chemical compound C12=CC=CC=C2C(=O)N(C)C2=CC=CN=C2N1CCCN1CCCC1 SKQUVSXNFDZXJA-UHFFFAOYSA-N 0.000 claims 3
RLGYLWUCPHLWAD-UHFFFAOYSA-N 6-methyl-11-(3-piperidin-1-ylpropyl)pyrido[3,2-c][1,5]benzodiazepin-5-one Chemical compound C12=NC=CC=C2C(=O)N(C)C2=CC=CC=C2N1CCCN1CCCCC1 RLGYLWUCPHLWAD-UHFFFAOYSA-N 0.000 claims 3
IYCWSTJQJJYPPD-UHFFFAOYSA-N 6-methyl-11-(3-pyrrolidin-1-ylpropyl)pyrido[3,2-c][1,5]benzodiazepin-5-one Chemical compound C12=NC=CC=C2C(=O)N(C)C2=CC=CC=C2N1CCCN1CCCC1 IYCWSTJQJJYPPD-UHFFFAOYSA-N 0.000 claims 3
FJZVJWDGGQSKDE-UHFFFAOYSA-N 6-methyl-11-[3-(methylamino)propyl]pyrido[3,2-c][1,5]benzodiazepin-5-one Chemical compound CN1C(=O)C2=CC=CN=C2N(CCCNC)C2=CC=CC=C21 FJZVJWDGGQSKDE-UHFFFAOYSA-N 0.000 claims 3
FTWYEPHYMXDOJU-UHFFFAOYSA-N 6-methyl-11-[3-(propan-2-ylamino)propyl]pyrido[3,2-c][1,5]benzodiazepin-5-one Chemical compound CN1C(=O)C2=CC=CN=C2N(CCCNC(C)C)C2=CC=CC=C21 FTWYEPHYMXDOJU-UHFFFAOYSA-N 0.000 claims 3
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 claims 3
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims 3
229910000041 hydrogen chloride Inorganic materials 0.000 claims 3
WTMFEPFCFKVODM-UHFFFAOYSA-N 11-[2-(diethylamino)ethyl]-6-methylpyrido[3,2-c][1,5]benzodiazepin-5-one Chemical compound CN1C(=O)C2=CC=CN=C2N(CCN(CC)CC)C2=CC=CC=C21 WTMFEPFCFKVODM-UHFFFAOYSA-N 0.000 claims 2
UGUFHIBGGZXRSH-UHFFFAOYSA-N 11-[2-(dimethylamino)ethyl]-6-methylpyrido[3,2-c][1,5]benzodiazepin-5-one Chemical compound CN1C(=O)C2=CC=CN=C2N(CCN(C)C)C2=CC=CC=C21 UGUFHIBGGZXRSH-UHFFFAOYSA-N 0.000 claims 2
QPAUBZVIWBHVRI-UHFFFAOYSA-N 11-[3-(dimethylamino)propyl]-6-methylpyrido[3,2-c][1,5]benzodiazepin-5-one Chemical compound CN1C(=O)C2=CC=CN=C2N(CCCN(C)C)C2=CC=CC=C21 QPAUBZVIWBHVRI-UHFFFAOYSA-N 0.000 claims 2
WCEDWMDESNWZAV-UHFFFAOYSA-N 11-[3-[ethyl(propan-2-yl)amino]propyl]-6-methylpyrido[3,2-c][1,5]benzodiazepin-5-one Chemical compound CN1C(=O)C2=CC=CN=C2N(CCCN(CC)C(C)C)C2=CC=CC=C21 WCEDWMDESNWZAV-UHFFFAOYSA-N 0.000 claims 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims 2
229910052736 halogen Inorganic materials 0.000 claims 2
150000002367 halogens Chemical group 0.000 claims 2
229910003002 lithium salt Inorganic materials 0.000 claims 2
159000000002 lithium salts Chemical class 0.000 claims 2
125000003386 piperidinyl group Chemical group 0.000 claims 2
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims 2
NWISBIWSLWEZSU-UHFFFAOYSA-N 11-[2-[di(propan-2-yl)amino]ethyl]-6-methylpyrido[3,2-c][1,5]benzodiazepin-5-one Chemical compound CN1C(=O)C2=CC=CN=C2N(CCN(C(C)C)C(C)C)C2=CC=CC=C21 NWISBIWSLWEZSU-UHFFFAOYSA-N 0.000 claims 1
SMEGFFNWIHEUQL-UHFFFAOYSA-N 11-[3-(dipropylamino)propyl]-6-methylpyrido[3,2-c][1,5]benzodiazepin-5-one Chemical compound CN1C(=O)C2=CC=CN=C2N(CCCN(CCC)CCC)C2=CC=CC=C21 SMEGFFNWIHEUQL-UHFFFAOYSA-N 0.000 claims 1
VTWZICMJJJQLKT-UHFFFAOYSA-N 3-(dimethylamino)propyl 4-methylbenzenesulfonate Chemical compound CN(C)CCCOS(=O)(=O)C1=CC=C(C)C=C1 VTWZICMJJJQLKT-UHFFFAOYSA-N 0.000 claims 1
UUNYBOOZTYTWLD-UHFFFAOYSA-N 3-chloro-n-ethyl-n-propan-2-ylpropan-1-amine Chemical compound CCN(C(C)C)CCCCl UUNYBOOZTYTWLD-UHFFFAOYSA-N 0.000 claims 1
230000000911 decarboxylating effect Effects 0.000 claims 1
WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 claims 1
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
XOVAMNMHLZQZJL-UHFFFAOYSA-N n-benzyl-3-chloro-n-methylpropan-1-amine Chemical compound ClCCCN(C)CC1=CC=CC=C1 XOVAMNMHLZQZJL-UHFFFAOYSA-N 0.000 claims 1
BWLFHTUZEZSUSH-UHFFFAOYSA-N n-benzyl-3-chloro-n-propan-2-ylpropan-1-amine Chemical compound ClCCCN(C(C)C)CC1=CC=CC=C1 BWLFHTUZEZSUSH-UHFFFAOYSA-N 0.000 claims 1
RIVIDPPYRINTTH-UHFFFAOYSA-N n-ethylpropan-2-amine Chemical compound CCNC(C)C RIVIDPPYRINTTH-UHFFFAOYSA-N 0.000 claims 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 claims 1
208000006673 asthma Diseases 0.000 abstract description 6
230000000144 pharmacologic effect Effects 0.000 abstract description 3
208000030603 inherited susceptibility to asthma Diseases 0.000 abstract description 2
239000008194 pharmaceutical composition Substances 0.000 abstract description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 40
239000000203 mixture Substances 0.000 description 37
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 28
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 24
YZPAKBGVJIVPEU-UHFFFAOYSA-N 1,2-benzodiazepin-6-one Chemical compound N1=NC=CC=C2C(=O)C=CC=C21 YZPAKBGVJIVPEU-UHFFFAOYSA-N 0.000 description 22
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
239000002480 mineral oil Substances 0.000 description 20
235000010446 mineral oil Nutrition 0.000 description 20
239000000243 solution Substances 0.000 description 19
239000004480 active ingredient Substances 0.000 description 16
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
230000000694 effects Effects 0.000 description 12
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 11
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 11
239000003921 oil Substances 0.000 description 11
239000008096 xylene Substances 0.000 description 11
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
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JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
229910052720 vanadium Inorganic materials 0.000 description 1
239000003981 vehicle Substances 0.000 description 1

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Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

CA227,479A 1974-02-20 1975-05-21 Pyridobenzodiazepinones, procede pour leur preparation et produits pharmaceutiques en contenant Expired CA1057286A (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19742408111 DE2408111C3 (de)	1973-02-20	1974-02-20	Faksimile-Empfänger

Publications (1)

Publication Number	Publication Date
CA1057286A true CA1057286A (fr)	1979-06-26

Family

ID=5907942

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA227,479A Expired CA1057286A (fr)	1974-02-20	1975-05-21	Pyridobenzodiazepinones, procede pour leur preparation et produits pharmaceutiques en contenant

Country Status (1)

Country	Link
CA (1)	CA1057286A (fr)

1975
- 1975-05-21 CA CA227,479A patent/CA1057286A/fr not_active Expired

Publication	Publication Date	Title
IL32853A (en)	1972-06-28	5,11-dihydro-6h-pyrido(2,3-b)-(1,4)benzodiazepine-6-ones substituted in 11-position and processes for the production thereof
AU600318B2 (en)	1990-08-09	Esters of hexahydro-8-hydroxy-2,6-methano-2h-quinolizin-3(4h)-one and related compounds
US3763183A (en)	1973-10-02	1,2,3,10,11,11a-hexahydro-5h-pyrrolo (2,1-c)(1,4)benzodiazepines
US4434171A (en)	1984-02-28	Dibenzazepine derivatives, pharmaceutical compositions containing them, and pharmaceutical methods using them
EP0028381B1 (fr)	1985-04-10	Azépinoindoles, procédé pour leur préparation et compositions pharmaceutiques les contenant
US4021557A (en)	1977-05-03	11-Aminoalkyl-pyridobenzodiazepinones and salts thereof
US3984556A (en)	1976-10-05	Alkyl-substituted-tricyclic quinazolinones for lowering blood pressure
US3833588A (en)	1974-09-03	Unsaturated-substituted tricyclic quinazolinones
GB2120662A (en)	1983-12-07	New azepinoindoles, their production and pharmaceutical compositions containing them
GB1569251A (en)	1980-06-11	Pyridobenzodiazepines
CA1057286A (fr)	1979-06-26	Pyridobenzodiazepinones, procede pour leur preparation et produits pharmaceutiques en contenant
US3860600A (en)	1975-01-14	Octahydropyrrido{8 2,1-c{9 {8 1,4{9 benzodiazepines
US3732212A (en)	1973-05-08	1,2,3,10,11,11a-hexahydro-5h-pyrrolo(2,1-c)(1,4)benzodiazepine-5,11-diones
FI80272C (fi)	1990-05-10	Foerfarande foer framstaellning av terapeutiskt anvaendbara pyrazolderivat med ergolinskelett samt deras syraadditionssalter.
US3859289A (en)	1975-01-07	Tricyclic pyrimidinones
US4167570A (en)	1979-09-11	2-Methyl-6-alkyl-11-aminoalkyl-6,11-dihydro-5H-pyrido(2,3-B)(1,5)benzodiazepin-5-ones and salts thereof
IE55232B1 (en)	1990-07-04	"n-(2-methoxyethyl)-noroxymorphone"
US3982000A (en)	1976-09-21	Alkyl-substituted-tricyclic quinazolinones as bronchodilators
US3496165A (en)	1970-02-17	Octahydro-3-benzazecines
CA1087182A (fr)	1980-10-07	1-piperazinyl-triazolo-thieno-1,4 diazepines substituees
US3969506A (en)	1976-07-13	Pharmacologically active tricyclic quinazolinones
CA1157018A (fr)	1983-11-15	Benzodiazepinones, procede de production, applications et medicaments les contenant
EP0001401A1 (fr)	1979-04-18	Dérivés de thiénobenzazépine, leur procédé de préparation et compositions pharmaceutiques les contenant
US3493560A (en)	1970-02-03	10,5 - (iminomethano) - 10,11 - dihydro - 5h-dibenzo(a,d)cyclohepten - 13-one and related compounds
US4694003A (en)	1987-09-15	Method of treating depression with 5-(aminoalkyl)-11-phenyl-5H-dibenzo(b,e)(1,4) diazepines