FI57259C - Foerfarande foer framstaellning av bronkolytiska och sekretolytiska 6,11-dihydro-6-metyl-5h-pyrido/2,3-b//1,5/benzodiazepin-5-oner och 5,11-dihydro-5-metyl-6h-pyrido/2,3-b//1,4/benzodiazepin-6-oner - Google Patents
Foerfarande foer framstaellning av bronkolytiska och sekretolytiska 6,11-dihydro-6-metyl-5h-pyrido/2,3-b//1,5/benzodiazepin-5-oner och 5,11-dihydro-5-metyl-6h-pyrido/2,3-b//1,4/benzodiazepin-6-oner Download PDFInfo
- Publication number
- FI57259C FI57259C FI751470A FI751470A FI57259C FI 57259 C FI57259 C FI 57259C FI 751470 A FI751470 A FI 751470A FI 751470 A FI751470 A FI 751470A FI 57259 C FI57259 C FI 57259C
- Authority
- FI
- Finland
- Prior art keywords
- pyrido
- dihydro
- methyl
- benzodiazepin
- general formula
- Prior art date
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- -1 hexamethyleneimino group Chemical group 0.000 claims description 48
- 150000001875 compounds Chemical class 0.000 claims description 36
- HCDXLUKTYFLIEM-UHFFFAOYSA-N 1,2-benzodiazepin-5-one Chemical compound O=C1C=CN=NC2=CC=CC=C12 HCDXLUKTYFLIEM-UHFFFAOYSA-N 0.000 claims description 25
- YZPAKBGVJIVPEU-UHFFFAOYSA-N 1,2-benzodiazepin-6-one Chemical class N1=NC=CC=C2C(=O)C=CC=C21 YZPAKBGVJIVPEU-UHFFFAOYSA-N 0.000 claims description 23
- MGDDXKBVXQCWER-UHFFFAOYSA-N pyrido[2,3-i][1,2]benzodiazepin-3-one Chemical compound N1=NC(=O)C=CC2=CC=C(N=CC=C3)C3=C21 MGDDXKBVXQCWER-UHFFFAOYSA-N 0.000 claims description 13
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 230000001813 broncholytic effect Effects 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
- 239000012442 inert solvent Substances 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 6
- 229940124630 bronchodilator Drugs 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
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- 239000002253 acid Substances 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
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- CJHKJXZMFZKGHI-UHFFFAOYSA-N 1h-pyrido[2,3-i][1,2]benzodiazepine Chemical class N1N=CC=CC2=CC=C(N=CC=C3)C3=C12 CJHKJXZMFZKGHI-UHFFFAOYSA-N 0.000 claims description 4
- ONUDKSCEPDVUPP-UHFFFAOYSA-N 6-methyl-11h-pyrido[3,2-c][1,5]benzodiazepin-5-one Chemical class O=C1N(C)C2=CC=CC=C2NC2=NC=CC=C21 ONUDKSCEPDVUPP-UHFFFAOYSA-N 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
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- 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 4
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- 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 description 1
- NYYRRBOMNHUCLB-UHFFFAOYSA-N 3-chloro-n,n-dimethylpropan-1-amine Chemical compound CN(C)CCCCl NYYRRBOMNHUCLB-UHFFFAOYSA-N 0.000 description 1
- FKXYUGSJUMXROI-UHFFFAOYSA-N 3-chloro-n,n-dipropylpropan-1-amine Chemical compound CCCN(CCC)CCCCl FKXYUGSJUMXROI-UHFFFAOYSA-N 0.000 description 1
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- 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 description 1
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- SFRAVXBSPHJEBZ-UHFFFAOYSA-N 6,11-dihydropyrido[3,2-c][1,5]benzodiazepin-5-one Chemical compound O=C1NC2=CC=CC=C2NC2=NC=CC=C12 SFRAVXBSPHJEBZ-UHFFFAOYSA-N 0.000 description 1
- CDEPTFSLSSGFDW-UHFFFAOYSA-N 6-methyl-11-(2-pyrrolidin-1-ylethyl)pyrido[3,2-c][1,5]benzodiazepin-5-one Chemical compound C12=NC=CC=C2C(=O)N(C)C2=CC=CC=C2N1CCN1CCCC1 CDEPTFSLSSGFDW-UHFFFAOYSA-N 0.000 description 1
- JIGPZVICWWQITP-UHFFFAOYSA-N 6-methyl-11-(2-pyrrolidin-1-ylethyl)pyrido[3,2-c][1,5]benzodiazepin-5-one;hydrochloride Chemical compound Cl.C12=NC=CC=C2C(=O)N(C)C2=CC=CC=C2N1CCN1CCCC1 JIGPZVICWWQITP-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- VMZMSVGSIHHEFF-UHFFFAOYSA-N 6-methyl-11-[2-(methylamino)ethyl]pyrido[3,2-c][1,5]benzodiazepin-5-one Chemical compound CN1C(=O)C2=CC=CN=C2N(CCNC)C2=CC=CC=C21 VMZMSVGSIHHEFF-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- BCUNDMHBKSYKEM-UHFFFAOYSA-N 6-methyl-11-[3-(propan-2-ylamino)propyl]pyrido[3,2-c][1,5]benzodiazepin-5-one;hydrochloride Chemical compound Cl.CN1C(=O)C2=CC=CN=C2N(CCCNC(C)C)C2=CC=CC=C21 BCUNDMHBKSYKEM-UHFFFAOYSA-N 0.000 description 1
- 101001053395 Arabidopsis thaliana Acid beta-fructofuranosidase 4, vacuolar Proteins 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- FCROTPJMJZQGNQ-UHFFFAOYSA-N C(C)N(CCCOC(=O)N1C2=C(C(N(C3=C1C=CC=C3)C)=O)C=CC=N2)CC Chemical compound C(C)N(CCCOC(=O)N1C2=C(C(N(C3=C1C=CC=C3)C)=O)C=CC=N2)CC FCROTPJMJZQGNQ-UHFFFAOYSA-N 0.000 description 1
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- 241000700199 Cavia porcellus Species 0.000 description 1
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- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 206010022998 Irritability Diseases 0.000 description 1
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
- 239000005662 Paraffin oil Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 241000906446 Theraps Species 0.000 description 1
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 1
- 229960004373 acetylcholine Drugs 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001414 amino alcohols Chemical class 0.000 description 1
- 230000001004 anti-acetylcholinic effect Effects 0.000 description 1
- 230000001088 anti-asthma Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 239000000168 bronchodilator agent Substances 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- OJYGBLRPYBAHRT-IPQSZEQASA-N chloralose Chemical compound O1[C@H](C(Cl)(Cl)Cl)O[C@@H]2[C@@H](O)[C@@H]([C@H](O)CO)O[C@@H]21 OJYGBLRPYBAHRT-IPQSZEQASA-N 0.000 description 1
- 229950009941 chloralose Drugs 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 230000002057 chronotropic effect Effects 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 235000011087 fumaric acid Nutrition 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- SIAPCJWMELPYOE-UHFFFAOYSA-N lithium hydride Chemical compound [LiH] SIAPCJWMELPYOE-UHFFFAOYSA-N 0.000 description 1
- 229910000103 lithium hydride Inorganic materials 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910001510 metal chloride Inorganic materials 0.000 description 1
- LMOINURANNBYCM-UHFFFAOYSA-N metaproterenol Chemical compound CC(C)NCC(O)C1=CC(O)=CC(O)=C1 LMOINURANNBYCM-UHFFFAOYSA-N 0.000 description 1
- 210000003097 mucus Anatomy 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 208000010125 myocardial infarction Diseases 0.000 description 1
- KIRSQOJWCUZWNA-UHFFFAOYSA-N n-(3-chloropropyl)-3-phenylpropan-1-amine Chemical compound ClCCCNCCCC1=CC=CC=C1 KIRSQOJWCUZWNA-UHFFFAOYSA-N 0.000 description 1
- JNTMWPCEVGHVML-UHFFFAOYSA-N n-benzyl-2-chloro-n-methylethanamine Chemical compound ClCCN(C)CC1=CC=CC=C1 JNTMWPCEVGHVML-UHFFFAOYSA-N 0.000 description 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 description 1
- 230000003533 narcotic effect Effects 0.000 description 1
- 229960002657 orciprenaline Drugs 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- 239000010970 precious metal Substances 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
- 239000002516 radical scavenger Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Substances [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 1
- 239000001119 stannous chloride Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 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 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/10—Expectorants
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pulmonology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2424811 | 1974-05-22 | ||
| DE2424811A DE2424811C3 (de) | 1974-05-22 | 1974-05-22 | Pyrido-benzodiazepinone, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI751470A7 FI751470A7 (en, 2012) | 1975-11-23 |
| FI57259B FI57259B (fi) | 1980-03-31 |
| FI57259C true FI57259C (fi) | 1980-07-10 |
Family
ID=5916217
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI751470A FI57259C (fi) | 1974-05-22 | 1975-05-20 | Foerfarande foer framstaellning av bronkolytiska och sekretolytiska 6,11-dihydro-6-metyl-5h-pyrido/2,3-b//1,5/benzodiazepin-5-oner och 5,11-dihydro-5-metyl-6h-pyrido/2,3-b//1,4/benzodiazepin-6-oner |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US4021557A (en, 2012) |
| JP (1) | JPS5224038B2 (en, 2012) |
| AT (1) | AT342058B (en, 2012) |
| BE (1) | BE829327A (en, 2012) |
| BG (3) | BG23901A3 (en, 2012) |
| CH (3) | CH617694A5 (en, 2012) |
| CS (1) | CS191264B2 (en, 2012) |
| DD (1) | DD117459A5 (en, 2012) |
| DE (1) | DE2424811C3 (en, 2012) |
| DK (1) | DK139724C (en, 2012) |
| ES (3) | ES437423A1 (en, 2012) |
| FI (1) | FI57259C (en, 2012) |
| FR (1) | FR2271831B1 (en, 2012) |
| GB (1) | GB1456627A (en, 2012) |
| HU (1) | HU173786B (en, 2012) |
| IE (1) | IE41244B1 (en, 2012) |
| IL (1) | IL47329A (en, 2012) |
| LU (1) | LU72560A1 (en, 2012) |
| NL (1) | NL7506008A (en, 2012) |
| NO (1) | NO141894C (en, 2012) |
| PH (1) | PH13405A (en, 2012) |
| PL (3) | PL98951B1 (en, 2012) |
| RO (2) | RO66914A (en, 2012) |
| SE (1) | SE421921B (en, 2012) |
| SU (3) | SU578878A3 (en, 2012) |
| YU (1) | YU130775A (en, 2012) |
| ZA (1) | ZA753272B (en, 2012) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2644121A1 (de) * | 1976-09-30 | 1978-04-06 | Thomae Gmbh Dr K | Neue pyridobenzodiazepinone, verfahren zu ihrer herstellung und diese enthaltende arzneimittel |
| EP0024582A1 (de) * | 1979-08-10 | 1981-03-11 | Byk Gulden Lomberg Chemische Fabrik GmbH | Benzodiazepinone, Verfahren zu ihrer Herstellung sowie sie enthaltende Arzneimittel |
| IL62792A (en) * | 1980-05-07 | 1985-02-28 | Byk Gulden Lomberg Chem Fab | Acylated dihydrothienodiazepinone compounds,process for their preparation,and medicaments containing them |
| US4381301A (en) * | 1980-05-07 | 1983-04-26 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Substituted tricyclic thieno compounds, their synthesis, their use, their compositions and their medicaments |
| SE448629B (sv) * | 1981-09-24 | 1987-03-09 | Robins Co Inc A H | Pyrido/1,4/bensodiazepiner |
| GB2110205B (en) * | 1981-09-24 | 1985-10-23 | Robins Co Inc A H | Methanone compounds and their use in the production of phenyl substituted pyrido]1,4 benzediazepiness |
| DE3643666A1 (de) * | 1986-12-20 | 1988-06-30 | Thomae Gmbh Dr K | Neue kondensierte diazepinone, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| ATE161535T1 (de) * | 1989-04-20 | 1998-01-15 | Boehringer Ingelheim Pharma | 6,11-dihydro-5h-pyrido(2,3-b)(1,5)benzodiazepin 5-one und thione und ihre verwendung für die vorbeugung oder behandlung von aids |
| CA2052946A1 (en) * | 1990-10-19 | 1992-04-20 | Karl G. Grozinger | Method for the preparation of 5,11-dihydro-6h-dipyrido ¬3,2-b:2', 3'-e| ¬1,4|diazepines |
| FR2850654A1 (fr) * | 2003-02-03 | 2004-08-06 | Servier Lab | Nouveaux derives d'azepines tricycliques, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| JP5020819B2 (ja) | 2004-07-16 | 2012-09-05 | プロテオシス・アーゲー | 細胞保護剤としての、ｐａｒｐ及びｓｉｒ調節活性を有するムスカリンアンタゴニスト |
| WO2010081825A2 (en) | 2009-01-13 | 2010-07-22 | Proteosys Ag | Pirenzepine as an agent in cancer treatment |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3316249A (en) * | 1967-04-25 | Part a.xmethyl n n-(z-diethylaminoethyl)-n-(z- nitrophenyl) anthranilate hydrochloride | ||
| FR1505795A (fr) * | 1965-12-17 | 1967-12-15 | Thomae Gmbh Dr K | Procédé pour fabriquer de nouvelles 11h-pyrido[2, 3-b][1, 5]benzodiazépine-5(6h)-ones substituées en position 11 |
| DE1795183B1 (de) * | 1968-08-20 | 1972-07-20 | Thomae Gmbh Dr K | 5,11-Dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-on-derivate und Arzneimittel |
| FI49509C (fi) * | 1968-08-20 | 1975-07-10 | Thomae Gmbh Dr K | Menetelmä farmakologisesti vaikuttavien 5-asemaan substituoitujen 5,10 -dihydro-11H-dibentso/b,e//1,4/deatsepiini-11-onien ja niiden suolojen valmistamiseksi. |
| AT327200B (de) * | 1972-09-06 | 1976-01-26 | Degussa | Verfahren zur herstellung von neuen aza-10,11-dihydro-5h-dibenzo (b,e)-(1,4) diazepinen sowie deren salzen |
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1974
- 1974-05-22 DE DE2424811A patent/DE2424811C3/de not_active Expired
-
1975
- 1975-04-09 AT AT267475A patent/AT342058B/de not_active IP Right Cessation
- 1975-04-23 US US05/570,805 patent/US4021557A/en not_active Expired - Lifetime
- 1975-04-25 PH PH17099A patent/PH13405A/en unknown
- 1975-05-03 ES ES437423A patent/ES437423A1/es not_active Expired
- 1975-05-15 SU SU7502133310A patent/SU578878A3/ru active
- 1975-05-20 BG BG030870A patent/BG23901A3/xx unknown
- 1975-05-20 CH CH641375A patent/CH617694A5/de not_active IP Right Cessation
- 1975-05-20 BG BG030032A patent/BG23541A3/xx unknown
- 1975-05-20 DD DD186145A patent/DD117459A5/xx unknown
- 1975-05-20 HU HU75TO1004A patent/HU173786B/hu unknown
- 1975-05-20 FI FI751470A patent/FI57259C/fi not_active IP Right Cessation
- 1975-05-20 BG BG030869A patent/BG24807A3/xx unknown
- 1975-05-21 CS CS753556A patent/CS191264B2/cs unknown
- 1975-05-21 PL PL1975180585A patent/PL98951B1/pl unknown
- 1975-05-21 PL PL1975193638A patent/PL98614B1/pl unknown
- 1975-05-21 BE BE156569A patent/BE829327A/xx unknown
- 1975-05-21 ZA ZA3272A patent/ZA753272B/xx unknown
- 1975-05-21 DK DK223175A patent/DK139724C/da not_active IP Right Cessation
- 1975-05-21 GB GB2198575A patent/GB1456627A/en not_active Expired
- 1975-05-21 NO NO751801A patent/NO141894C/no unknown
- 1975-05-21 JP JP50060889A patent/JPS5224038B2/ja not_active Expired
- 1975-05-21 YU YU01307/75A patent/YU130775A/xx unknown
- 1975-05-21 RO RO7582297A patent/RO66914A/ro unknown
- 1975-05-21 SE SE7505796A patent/SE421921B/xx unknown
- 1975-05-21 RO RO7591013A patent/RO71575A/ro unknown
- 1975-05-21 PL PL1975193639A patent/PL100079B1/pl unknown
- 1975-05-21 IL IL47329A patent/IL47329A/xx unknown
- 1975-05-22 IE IE1146/75A patent/IE41244B1/xx unknown
- 1975-05-22 LU LU72560A patent/LU72560A1/xx unknown
- 1975-05-22 FR FR7515960A patent/FR2271831B1/fr not_active Expired
- 1975-05-22 NL NL7506008A patent/NL7506008A/xx not_active Application Discontinuation
- 1975-10-08 ES ES441591A patent/ES441591A1/es not_active Expired
- 1975-10-08 ES ES441592A patent/ES441592A1/es not_active Expired
-
1976
- 1976-03-11 SU SU7602331204A patent/SU567407A3/ru active
- 1976-03-11 SU SU762331952A patent/SU587864A3/ru active
-
1979
- 1979-04-20 CH CH377979A patent/CH617698A5/de not_active IP Right Cessation
- 1979-04-20 CH CH378079A patent/CH617699A5/de not_active IP Right Cessation
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: DR. KARL THOMAE GESELLSCHAFT |