DD283141A5 - Verfahren zur herstellung kondensierter diazepinone - Google Patents

Verfahren zur herstellung kondensierter diazepinone Download PDF

Info

Publication number: DD283141A5
Authority: DD; German Democratic Republic
Prior art keywords: general formula; group; atom; dihydro; carbon atoms
Prior art date: 1987-10-23

Application number

DD88320971A

Other languages

German (de)

English (en)

Inventor

Wolfgang Eberlein

Wolfhard Engel

Guenter Trummlitz

Gerhard Mihm

Norbert Mayer

Henri Doods

Original Assignee

��K@��@��@��@��@��@��k��

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.)

1987-10-23

Filing date

1988-10-21

Publication date

1990-10-03

1988-10-21 Application filed by ��K@��@��@��@��@��@��k�� filed Critical ��K@��@��@��@��@��@��k��

1990-10-03 Publication of DD283141A5 publication Critical patent/DD283141A5/de

Links

DHZYXWMZLAKTQV-UHFFFAOYSA-N diazepin-3-one Chemical compound O=C1C=CC=CN=N1 DHZYXWMZLAKTQV-UHFFFAOYSA-N 0.000 title claims abstract description 17
238000004519 manufacturing process Methods 0.000 title abstract description 8
150000001875 compounds Chemical class 0.000 claims abstract description 34
239000002904 solvent Substances 0.000 claims abstract description 24
238000000034 method Methods 0.000 claims abstract description 13
238000002360 preparation method Methods 0.000 claims abstract description 10
150000003335 secondary amines Chemical class 0.000 claims abstract description 7
238000009835 boiling Methods 0.000 claims abstract description 4
125000005252 haloacyl group Chemical group 0.000 claims abstract description 4
239000011541 reaction mixture Substances 0.000 claims abstract description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 45
-1 1,2- Ethylene group Chemical group 0.000 claims description 35
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 33
239000002253 acid Substances 0.000 claims description 22
125000004432 carbon atom Chemical group C* 0.000 claims description 22
239000000203 mixture Substances 0.000 claims description 22
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 19
229910052801 chlorine Inorganic materials 0.000 claims description 16
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 16
239000000460 chlorine Substances 0.000 claims description 15
238000006243 chemical reaction Methods 0.000 claims description 14
150000003839 salts Chemical class 0.000 claims description 14
239000003054 catalyst Substances 0.000 claims description 13
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
239000001257 hydrogen Substances 0.000 claims description 10
229910052739 hydrogen Inorganic materials 0.000 claims description 10
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 9
125000000217 alkyl group Chemical group 0.000 claims description 9
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 8
235000019253 formic acid Nutrition 0.000 claims description 8
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 7
239000011737 fluorine Substances 0.000 claims description 7
229910052731 fluorine Inorganic materials 0.000 claims description 7
150000008064 anhydrides Chemical class 0.000 claims description 6
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 6
125000001309 chloro group Chemical group Cl* 0.000 claims description 6
125000000753 cycloalkyl group Chemical group 0.000 claims description 6
239000012442 inert solvent Substances 0.000 claims description 6
125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
229910052763 palladium Inorganic materials 0.000 claims description 6
241001465754 Metazoa Species 0.000 claims description 5
150000007513 acids Chemical class 0.000 claims description 5
125000002252 acyl group Chemical group 0.000 claims description 5
125000001931 aliphatic group Chemical group 0.000 claims description 5
229910052799 carbon Inorganic materials 0.000 claims description 5
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 5
239000003610 charcoal Substances 0.000 claims description 5
150000002148 esters Chemical class 0.000 claims description 5
238000007327 hydrogenolysis reaction Methods 0.000 claims description 5
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 5
229910052757 nitrogen Inorganic materials 0.000 claims description 5
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 4
150000001412 amines Chemical class 0.000 claims description 4
150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
150000004292 cyclic ethers Chemical class 0.000 claims description 4
150000004820 halides Chemical class 0.000 claims description 4
229910052760 oxygen Inorganic materials 0.000 claims description 4
239000001301 oxygen Substances 0.000 claims description 4
229910052717 sulfur Inorganic materials 0.000 claims description 4
125000004434 sulfur atom Chemical group 0.000 claims description 4
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 3
150000001298 alcohols Chemical class 0.000 claims description 3
150000001735 carboxylic acids Chemical class 0.000 claims description 3
229910052740 iodine Inorganic materials 0.000 claims description 3
150000007522 mineralic acids Chemical class 0.000 claims description 3
150000007524 organic acids Chemical class 0.000 claims description 3
235000005985 organic acids Nutrition 0.000 claims description 3
YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 claims description 3
229920006395 saturated elastomer Polymers 0.000 claims description 3
239000007868 Raney catalyst Substances 0.000 claims description 2
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims description 2
229910000564 Raney nickel Inorganic materials 0.000 claims description 2
150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 2
239000011230 binding agent Substances 0.000 claims description 2
229910052794 bromium Inorganic materials 0.000 claims description 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
229910017052 cobalt Inorganic materials 0.000 claims description 2
239000010941 cobalt Substances 0.000 claims description 2
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
229910052751 metal Inorganic materials 0.000 claims description 2
239000002184 metal Substances 0.000 claims description 2
150000002739 metals Chemical class 0.000 claims description 2
239000011707 mineral Substances 0.000 claims description 2
125000002950 monocyclic group Chemical group 0.000 claims description 2
125000004430 oxygen atom Chemical group O* 0.000 claims description 2
230000000737 periodic effect Effects 0.000 claims description 2
239000003880 polar aprotic solvent Substances 0.000 claims description 2
150000003512 tertiary amines Chemical class 0.000 claims description 2
ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 claims description 2
TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 claims 2
241000251730 Chondrichthyes Species 0.000 claims 1
230000009089 cytolysis Effects 0.000 claims 1
150000002170 ethers Chemical class 0.000 claims 1
PTMFUWGXPRYYMC-UHFFFAOYSA-N triethylazanium;formate Chemical compound OC=O.CCN(CC)CC PTMFUWGXPRYYMC-UHFFFAOYSA-N 0.000 claims 1
208000006218 bradycardia Diseases 0.000 abstract description 6
239000003814 drug Substances 0.000 abstract description 6
230000036471 bradycardia Effects 0.000 abstract description 4
230000002401 inhibitory effect Effects 0.000 abstract description 4
230000001078 anti-cholinergic effect Effects 0.000 abstract description 3
230000027119 gastric acid secretion Effects 0.000 abstract description 3
230000002911 mydriatic effect Effects 0.000 abstract description 2
230000008569 process Effects 0.000 abstract description 2
230000009286 beneficial effect Effects 0.000 abstract 1
150000004908 diazepines Chemical class 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 64
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 60
239000013078 crystal Substances 0.000 description 35
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 description 25
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 23
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 16
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 16
239000000126 substance Substances 0.000 description 16
KSSXNHGPIDAUAS-UHFFFAOYSA-N 1,4-benzodiazepin-6-one Chemical compound N1=CC=NC=C2C(=O)C=CC=C21 KSSXNHGPIDAUAS-UHFFFAOYSA-N 0.000 description 15
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 11
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 description 11
239000002585 base Substances 0.000 description 10
239000000243 solution Substances 0.000 description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 9
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 8
RMBZFWLMYVPNGI-UHFFFAOYSA-N 11-(2-chloroacetyl)-5h-pyrido[2,3-b][1,4]benzodiazepin-6-one Chemical compound O=C1NC2=CC=CN=C2N(C(=O)CCl)C2=CC=CC=C21 RMBZFWLMYVPNGI-UHFFFAOYSA-N 0.000 description 7
238000005160 1H NMR spectroscopy Methods 0.000 description 7
241000700159 Rattus Species 0.000 description 7
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 7
230000000694 effects Effects 0.000 description 7
210000000056 organ Anatomy 0.000 description 7
239000000829 suppository Substances 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 6
229960004373 acetylcholine Drugs 0.000 description 6
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
150000003254 radicals Chemical class 0.000 description 6
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 5
239000013543 active substance Substances 0.000 description 5
230000005764 inhibitory process Effects 0.000 description 5
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
ZVAPWJGRRUHKGP-UHFFFAOYSA-N 1h-1,5-benzodiazepine Chemical compound N1C=CC=NC2=CC=CC=C12 ZVAPWJGRRUHKGP-UHFFFAOYSA-N 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
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230000009471 action Effects 0.000 description 4
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238000005917 acylation reaction Methods 0.000 description 4
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230000027455 binding Effects 0.000 description 4
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
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HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
PCDGHYIREOOHMR-UHFFFAOYSA-N n,n-diethyl-4-piperidin-4-ylbutan-1-amine Chemical compound CCN(CC)CCCCC1CCNCC1 PCDGHYIREOOHMR-UHFFFAOYSA-N 0.000 description 4
230000000144 pharmacologic effect Effects 0.000 description 4
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
230000028327 secretion Effects 0.000 description 4
239000000741 silica gel Substances 0.000 description 4
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238000003786 synthesis reaction Methods 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 4
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 3
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 3
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241000700199 Cavia porcellus Species 0.000 description 3
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
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238000004440 column chromatography Methods 0.000 description 3
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 3
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QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
230000009871 nonspecific binding Effects 0.000 description 1
239000002245 particle Substances 0.000 description 1
230000002093 peripheral effect Effects 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
239000012071 phase Substances 0.000 description 1
229960001416 pilocarpine Drugs 0.000 description 1
125000003386 piperidinyl group Chemical group 0.000 description 1
RMHMFHUVIITRHF-UHFFFAOYSA-N pirenzepine Chemical compound C1CN(C)CCN1CC(=O)N1C2=NC=CC=C2NC(=O)C2=CC=CC=C21 RMHMFHUVIITRHF-UHFFFAOYSA-N 0.000 description 1
229960004633 pirenzepine Drugs 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
235000011181 potassium carbonates Nutrition 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
238000000159 protein binding assay Methods 0.000 description 1
239000002287 radioligand Substances 0.000 description 1
238000001525 receptor binding assay Methods 0.000 description 1
239000013558 reference substance Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
210000003296 saliva Anatomy 0.000 description 1
208000026451 salivation Diseases 0.000 description 1
238000007127 saponification reaction Methods 0.000 description 1
230000007017 scission Effects 0.000 description 1
210000002460 smooth muscle Anatomy 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
235000009518 sodium iodide Nutrition 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
230000002048 spasmolytic effect Effects 0.000 description 1
230000009870 specific binding Effects 0.000 description 1
238000013222 sprague-dawley male rat Methods 0.000 description 1
230000001954 sterilising effect Effects 0.000 description 1
238000004659 sterilization and disinfection Methods 0.000 description 1
210000002784 stomach Anatomy 0.000 description 1
238000003860 storage Methods 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 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
MEYTUZLAONGIPB-UHFFFAOYSA-N tris[2,5-di(propan-2-yl)phenyl]phosphane Chemical compound CC(C)C1=CC=C(C(C)C)C(P(C=2C(=CC=C(C=2)C(C)C)C(C)C)C=2C(=CC=C(C=2)C(C)C)C(C)C)=C1 MEYTUZLAONGIPB-UHFFFAOYSA-N 0.000 description 1
210000000626 ureter Anatomy 0.000 description 1
238000003828 vacuum filtration Methods 0.000 description 1
229910052720 vanadium Inorganic materials 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/06—Antiarrhythmics
- 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
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—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)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
Engineering & Computer Science (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (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)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

DD88320971A 1987-10-23 1988-10-21 Verfahren zur herstellung kondensierter diazepinone DD283141A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19873735895 DE3735895A1 (de)	1987-10-23	1987-10-23	Kondensierte diazepinone, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel

Publications (1)

Publication Number	Publication Date
DD283141A5 true DD283141A5 (de)	1990-10-03

Family

ID=6338927

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD88320971A DD283141A5 (de)	1987-10-23	1988-10-21	Verfahren zur herstellung kondensierter diazepinone

Country Status (16)

Country	Link
US (1)	US5175158A (fr)
EP (1)	EP0312895A3 (fr)
JP (1)	JPH0660172B2 (fr)
KR (1)	KR890006646A (fr)
AU (1)	AU609530B2 (fr)
CA (1)	CA1321996C (fr)
DD (1)	DD283141A5 (fr)
DE (1)	DE3735895A1 (fr)
DK (1)	DK586188A (fr)
FI (1)	FI87073C (fr)
HU (1)	HU199471B (fr)
IL (1)	IL88121A (fr)
NO (1)	NO167146C (fr)
NZ (1)	NZ226681A (fr)
PT (1)	PT88808B (fr)
ZA (1)	ZA887877B (fr)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3820347A1 (de) *	1988-06-15	1989-12-21	Thomae Gmbh Dr K	Verwendung von in 11-stellung substituierten 5,11-dihydro-6h-pyrido(2,3-b) (1,4)benzodiazepin-6-onen zur behandlung von bradycardien und bradyarrhythmien in der human- und veterinaermedizin
US5366972A (en) *	1989-04-20	1994-11-22	Boehringer Ingelheim Pharmaceuticals, Inc.	5,11-dihydro-6H-dipyrido(3,2-B:2',3'-E)(1,4)diazepines and their use in the prevention or treatment of HIV infection
CA2019812C (fr) *	1989-06-28	2000-11-21	Gunther Schmidt (Deceased)	Nouveau 5,11-dihydro-6h-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-ones et leur utilisation dans la prevention et le traitement du sida
CA2030056C (fr) *	1989-11-17	1995-10-17	Karl D. Hargrave	5,11-dihydro-6h-dipyrido[3,2-b:2',3'-e][1,4]diazepines et leur utilisation pour la prevention ou le traitement de l'infection par le hiv
IE912239A1 (en) *	1990-07-24	1992-01-29	Akzo Nv	Tetrahydropyridinyldibenzazepine derivatives
DE4112014A1 (de) *	1991-04-12	1992-10-15	Thomae Gmbh Dr K	Kondensierte diazepinone, verfahren zu ihrer herstellung und diese verbindungen enthaltende mittel zur behandlung von erkrankungen des zentralnervensystems und zur foerderung der cerebralen durchblutung
US5610155A (en) *	1992-04-09	1997-03-11	Dr. Karl Thomae Gmbh	Condensed diazepinones, processes for preparing them and agents containing these compounds for treating diseases of the central nervous system and for promoting cerebral blood circulation
WO1994022861A1 (fr) *	1993-04-05	1994-10-13	Pharmaceutical Discovery Corporation	PYRIDO[2,3-b][1,4]BENZODIAZEPINONES EN TANT QUE LIGAND DE RECEPTEUR M2 POUR LE TRAITEMENT DE TROUBLES NEUROLOGIQUES
US6316623B1 (en) *	1998-08-21	2001-11-13	Isis Pharmaceuticals, Inc.	Ethylenediamine compound libraries
JPWO2004011430A1 (ja) *	2002-07-25	2005-11-24	アステラス製薬株式会社	ナトリウムチャネル阻害剤

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3235795A1 (de) *	1982-09-28	1984-03-29	Dr. Karl Thomae Gmbh, 7950 Biberach	Neues verfahren zur herstellung von 5,11-dihydro-11-((4-methyl-1-piperazinyl)- acetyl)- 6h-pyrido(2,3-b)(1,4)- benzodiazepin-6-on
DE3409237A1 (de) *	1984-03-14	1985-09-19	Dr. Karl Thomae Gmbh, 7950 Biberach	Kondensierte diazepinone, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel

1987
- 1987-10-23 DE DE19873735895 patent/DE3735895A1/de not_active Ceased
1988
- 1988-10-12 EP EP88116886A patent/EP0312895A3/fr not_active Ceased
- 1988-10-19 CA CA000580585A patent/CA1321996C/fr not_active Expired - Fee Related
- 1988-10-20 PT PT88808A patent/PT88808B/pt not_active IP Right Cessation
- 1988-10-21 NZ NZ226681A patent/NZ226681A/en unknown
- 1988-10-21 JP JP63265926A patent/JPH0660172B2/ja not_active Expired - Lifetime
- 1988-10-21 ZA ZA887877A patent/ZA887877B/xx unknown
- 1988-10-21 HU HU885438A patent/HU199471B/hu not_active IP Right Cessation
- 1988-10-21 DD DD88320971A patent/DD283141A5/de not_active IP Right Cessation
- 1988-10-21 DK DK586188A patent/DK586188A/da not_active Application Discontinuation
- 1988-10-21 IL IL88121A patent/IL88121A/xx not_active IP Right Cessation
- 1988-10-21 FI FI884863A patent/FI87073C/fi not_active IP Right Cessation
- 1988-10-21 NO NO884698A patent/NO167146C/no unknown
- 1988-10-21 AU AU24122/88A patent/AU609530B2/en not_active Ceased
- 1988-10-22 KR KR1019880013812A patent/KR890006646A/ko not_active Ceased
- 1988-10-24 US US07/261,950 patent/US5175158A/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
ZA887877B (en)	1990-06-27
FI87073C (fi)	1992-11-25
NO167146B (no)	1991-07-01
FI87073B (fi)	1992-08-14
IL88121A (en)	1993-06-10
DE3735895A1 (de)	1989-05-03
DK586188D0 (da)	1988-10-21
IL88121A0 (en)	1989-06-30
JPH0660172B2 (ja)	1994-08-10
EP0312895A2 (fr)	1989-04-26
AU2412288A (en)	1989-04-27
DK586188A (da)	1989-04-24
EP0312895A3 (fr)	1990-08-16
CA1321996C (fr)	1993-09-07
HUT48629A (en)	1989-06-28
NO884698L (no)	1989-04-24
HU199471B (en)	1990-02-28
US5175158A (en)	1992-12-29
AU609530B2 (en)	1991-05-02
NO167146C (no)	1991-10-09
NO884698D0 (no)	1988-10-21
JPH01230580A (ja)	1989-09-14
NZ226681A (en)	1991-06-25
FI884863A7 (fi)	1989-04-24
PT88808B (pt)	1993-01-29
FI884863A0 (fi)	1988-10-21
KR890006646A (ko)	1989-06-15

Legal Events

Date	Code	Title	Description
1995-06-08	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
EP0156191B1 (fr)	1989-07-19	Diazépinones condensées, procédé pour leur préparation et médicaments contenant les composés
DD283141A5 (de)	1990-10-03	Verfahren zur herstellung kondensierter diazepinone
EP0254955B1 (fr)	1992-05-27	Pyrido[2,3-b][1,4]benzodiazépin-6-ones substituées, leur procédé de préparation et médicaments contenant ces composés
EP0306698B1 (fr)	1992-03-25	Diazépinones condensées, procédés pour leur préparation et médicament contenant ces composés
EP0085899B1 (fr)	1986-10-29	Pyridobenzodiazépinones, procédé pour leur préparation et compositions pharmaceutiques les contenant
EP0508370B1 (fr)	1996-07-03	Diazépinones condensées, procédé pour leur préparation et compositions les contenant pour le traitement de maladies du système nerveux central et pour augmenter la perfusion cérébrale
DE3204157A1 (de)	1983-08-11	Substituierte dibenzodiazepinone, verfahren zu ihrer herstellung und sie enthaltende arzneimittel
EP0273239B1 (fr)	1991-03-06	Diazépinones condensés, leur procédé de préparation et médicaments les contenant
DD284016A5 (de)	1990-10-31	Verfahren zur herstellung von kondensierten diazepinonen
EP0345629B1 (fr)	1992-09-16	Diazépinones condensées, procédé pour leur préparation et médicaments les contenant
EP0344543A2 (fr)	1989-12-06	Diazépinones condensées, procédé pour leur préparation et médicaments les contenant
EP0086982A1 (fr)	1983-08-31	Thienobenzodiazépinones substituées, procédé pour leur fabrication et médicaments les contenant
DE3802334A1 (de)	1989-08-10	Neue kondensierte diazepinone, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
DD284015A5 (de)	1990-10-31	Verfahren zur herstellung von kondensierten diazepinonen
US4931436A (en)	1990-06-05	Condensed diazepinones, processes for preparing them and pharmaceutical compositions containing these compounds
DD251982A5 (de)	1987-12-02	Verfahren zur herstellung von neuen in 11-stellung substituierten 5,11-dihydro-6h-pyride-(2,3-b)(1,4) benzodiazipin-6-onen
DD299307A5 (de)	1992-04-09	Kondensierte diazepine, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
EP0086980A1 (fr)	1983-08-31	Dibenzodiazépinones substituées, procédé pour leur fabrication et médicaments contenant ces composés