NO127447B - - Google Patents
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- Publication number
- NO127447B NO127447B NO02815/70A NO281570A NO127447B NO 127447 B NO127447 B NO 127447B NO 02815/70 A NO02815/70 A NO 02815/70A NO 281570 A NO281570 A NO 281570A NO 127447 B NO127447 B NO 127447B
- Authority
- NO
- Norway
- Prior art keywords
- dihydro
- diazepin
- dibenzo
- diallylamine
- isopropanol
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 24
- DYUWTXWIYMHBQS-UHFFFAOYSA-N n-prop-2-enylprop-2-en-1-amine Chemical compound C=CCNCC=C DYUWTXWIYMHBQS-UHFFFAOYSA-N 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 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
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 41
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 22
- 238000002844 melting Methods 0.000 description 17
- 230000008018 melting Effects 0.000 description 17
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 16
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 241000700159 Rattus Species 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 7
- 241001465754 Metazoa Species 0.000 description 7
- 230000002401 inhibitory effect Effects 0.000 description 7
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 230000028327 secretion Effects 0.000 description 6
- 238000000354 decomposition reaction Methods 0.000 description 5
- -1 for example Substances 0.000 description 5
- 239000002585 base Substances 0.000 description 4
- 210000004051 gastric juice Anatomy 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000000155 melt Substances 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- KSSXNHGPIDAUAS-UHFFFAOYSA-N 1,4-benzodiazepin-6-one Chemical compound N1=CC=NC=C2C(=O)C=CC=C21 KSSXNHGPIDAUAS-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002026 chloroform extract Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000001530 fumaric acid Substances 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 210000002784 stomach Anatomy 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- JZUFKLXOESDKRF-UHFFFAOYSA-N Chlorothiazide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NCNS2(=O)=O JZUFKLXOESDKRF-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 206010042220 Stress ulcer Diseases 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 208000025865 Ulcer Diseases 0.000 description 2
- 206010052428 Wound Diseases 0.000 description 2
- 208000027418 Wounds and injury Diseases 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- 208000000718 duodenal ulcer Diseases 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000012433 hydrogen halide Substances 0.000 description 2
- 229910000039 hydrogen halide Inorganic materials 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 239000002504 physiological saline solution Substances 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- IHQCAIBFGQAEHI-UHFFFAOYSA-N 11-(2-chloroacetyl)-5-methylbenzo[b][1,4]benzodiazepin-6-one Chemical compound O=C1N(C)C2=CC=CC=C2N(C(=O)CCl)C2=CC=CC=C21 IHQCAIBFGQAEHI-UHFFFAOYSA-N 0.000 description 1
- OYGJCGQSFROSHD-UHFFFAOYSA-N 11-(2-chloroacetyl)-5h-benzo[b][1,4]benzodiazepin-6-one Chemical compound N1C(=O)C2=CC=CC=C2N(C(=O)CCl)C2=CC=CC=C21 OYGJCGQSFROSHD-UHFFFAOYSA-N 0.000 description 1
- 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 1
- QPHUWSLVGFCPLN-UHFFFAOYSA-N 11-(3-chloropropanoyl)-5-methylbenzo[b][1,4]benzodiazepin-6-one Chemical compound O=C1N(C)C2=CC=CC=C2N(C(=O)CCCl)C2=CC=CC=C21 QPHUWSLVGFCPLN-UHFFFAOYSA-N 0.000 description 1
- LEGYNZZRECSDDJ-UHFFFAOYSA-N 11-(3-chloropropanoyl)-5h-benzo[b][1,4]benzodiazepin-6-one Chemical compound N1C(=O)C2=CC=CC=C2N(C(=O)CCCl)C2=CC=CC=C21 LEGYNZZRECSDDJ-UHFFFAOYSA-N 0.000 description 1
- LGZOSKMLOODXAV-UHFFFAOYSA-N 11-(3-chloropropanoyl)-5h-pyrido[2,3-b][1,4]benzodiazepin-6-one Chemical compound O=C1NC2=CC=CN=C2N(C(=O)CCCl)C2=CC=CC=C21 LGZOSKMLOODXAV-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- WQLBHCAKRWHYNG-UHFFFAOYSA-N 3-chloro-11-(2-chloroacetyl)-5h-benzo[b][1,4]benzodiazepin-6-one Chemical compound N1C(=O)C2=CC=CC=C2N(C(=O)CCl)C2=CC=C(Cl)C=C21 WQLBHCAKRWHYNG-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- DRODPUMMRSYAJW-UHFFFAOYSA-N 8-chloro-11-(2-chloropropanoyl)-5H-benzo[b][1,4]benzodiazepin-6-one Chemical compound ClC1=CC2=C(N(C3=C(NC2=O)C=CC=C3)C(C(C)Cl)=O)C=C1 DRODPUMMRSYAJW-UHFFFAOYSA-N 0.000 description 1
- LJYVIIWSTMUPQD-UHFFFAOYSA-N 8-chloro-11-(3-chloropropanoyl)-5-methylbenzo[b][1,4]benzodiazepin-6-one Chemical compound O=C1N(C)C2=CC=CC=C2N(C(=O)CCCl)C2=CC=C(Cl)C=C21 LJYVIIWSTMUPQD-UHFFFAOYSA-N 0.000 description 1
- HDZZIBOAYMLNFO-UHFFFAOYSA-N 8-chloro-11-(3-chloropropanoyl)-5h-benzo[b][1,4]benzodiazepin-6-one Chemical compound N1C(=O)C2=CC(Cl)=CC=C2N(C(=O)CCCl)C2=CC=CC=C21 HDZZIBOAYMLNFO-UHFFFAOYSA-N 0.000 description 1
- KKONBTKPCIKQMC-UHFFFAOYSA-N 9-chloro-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(Cl)=CC=C21 KKONBTKPCIKQMC-UHFFFAOYSA-N 0.000 description 1
- 208000028048 Accommodation disease Diseases 0.000 description 1
- 206010002091 Anaesthesia Diseases 0.000 description 1
- 229930003347 Atropine Natural products 0.000 description 1
- 241000700199 Cavia porcellus Species 0.000 description 1
- PRYCESJTHATKNQ-UHFFFAOYSA-N ClC1=CC2=C(N(C3=C(N(C2=O)C)C=CC=C3)C(CCl)=O)C=C1 Chemical compound ClC1=CC2=C(N(C3=C(N(C2=O)C)C=CC=C3)C(CCl)=O)C=C1 PRYCESJTHATKNQ-UHFFFAOYSA-N 0.000 description 1
- CKIANDRUVDGKCO-UHFFFAOYSA-N ClCCC(=O)N1C2=C(N(C(C3=C1C=CC=C3)=O)C)C=CC=N2 Chemical compound ClCCC(=O)N1C2=C(N(C(C3=C1C=CC=C3)=O)C)C=CC=N2 CKIANDRUVDGKCO-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
- RKUNBYITZUJHSG-UHFFFAOYSA-N Hyosciamin-hydrochlorid Natural products CN1C(C2)CCC1CC2OC(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-UHFFFAOYSA-N 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 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
- HOBWAPHTEJGALG-JKCMADFCSA-N [(1r,5s)-8-methyl-8-azoniabicyclo[3.2.1]octan-3-yl] 3-hydroxy-2-phenylpropanoate;sulfate Chemical compound [O-]S([O-])(=O)=O.C([C@H]1CC[C@@H](C2)[NH+]1C)C2OC(=O)C(CO)C1=CC=CC=C1.C([C@H]1CC[C@@H](C2)[NH+]1C)C2OC(=O)C(CO)C1=CC=CC=C1 HOBWAPHTEJGALG-JKCMADFCSA-N 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
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 230000001078 anti-cholinergic effect Effects 0.000 description 1
- 230000000767 anti-ulcer Effects 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 229960000396 atropine Drugs 0.000 description 1
- RKUNBYITZUJHSG-SPUOUPEWSA-N atropine Chemical compound O([C@H]1C[C@H]2CC[C@@H](C1)N2C)C(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-SPUOUPEWSA-N 0.000 description 1
- 229960002028 atropine sulfate Drugs 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 210000001072 colon Anatomy 0.000 description 1
- 239000003179 convulsant agent Substances 0.000 description 1
- 239000007799 cork Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- UZVGSSNIUNSOFA-UHFFFAOYSA-N dibenzofuran-1-carboxylic acid Chemical compound O1C2=CC=CC=C2C2=C1C=CC=C2C(=O)O UZVGSSNIUNSOFA-UHFFFAOYSA-N 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- UYXAWHWODHRRMR-UHFFFAOYSA-N hexobarbital Chemical compound O=C1N(C)C(=O)NC(=O)C1(C)C1=CCCCC1 UYXAWHWODHRRMR-UHFFFAOYSA-N 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 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
- 238000004519 manufacturing process Methods 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 230000008855 peristalsis Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 210000001187 pylorus Anatomy 0.000 description 1
- QYETZOYLEWPRIX-UHFFFAOYSA-N pyrido[2,3-b][1,4]benzodiazepin-6-one Chemical compound O=C1N=C2C=CC=NC2=NC2=CC=CC=C12 QYETZOYLEWPRIX-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 210000003296 saliva Anatomy 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 230000002048 spasmolytic effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 210000001562 sternum Anatomy 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 231100000041 toxicology testing Toxicity 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
- 230000036269 ulceration Effects 0.000 description 1
- 238000005303 weighing Methods 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K33/00—Medicinal preparations containing inorganic active ingredients
- A61K33/06—Aluminium, calcium or magnesium; Compounds thereof, e.g. clay
- A61K33/12—Magnesium silicate
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19691936670 DE1936670C3 (de) | 1969-07-18 | S-Diallylaminoalkanoyl-SJO-dihydro-11H-dibenzo eckige Klammer auf b,e eckige Klammer zu- eckige Klammer auf 1,4 eckige Klammer zu diazepin-11-onderivate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO127447B true NO127447B (de) | 1973-06-25 |
Family
ID=5740245
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO02815/70A NO127447B (de) | 1969-07-18 | 1970-07-17 |
Country Status (20)
| Country | Link |
|---|---|
| US (2) | US3691159A (de) |
| AT (1) | AT298495B (de) |
| BE (1) | BE753664A (de) |
| BG (1) | BG17802A3 (de) |
| CH (1) | CH530988A (de) |
| CS (1) | CS164864B2 (de) |
| DK (1) | DK135285B (de) |
| ES (1) | ES381898A1 (de) |
| FI (1) | FI50242C (de) |
| FR (1) | FR2059530B1 (de) |
| GB (1) | GB1265467A (de) |
| IE (1) | IE34393B1 (de) |
| IL (1) | IL34947A (de) |
| NL (1) | NL165933C (de) |
| NO (1) | NO127447B (de) |
| PL (1) | PL79758B1 (de) |
| RO (1) | RO55559A (de) |
| SE (1) | SE380800B (de) |
| YU (1) | YU181070A (de) |
| ZA (1) | ZA704861B (de) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2724478C2 (de) * | 1977-05-31 | 1986-05-22 | Dr. Karl Thomae Gmbh, 7950 Biberach | 5,11-Dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-on-derivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel |
| DE2724501A1 (de) * | 1977-05-31 | 1978-12-21 | Thomae Gmbh Dr K | Neue, in 11-stellung substituierte 5,11-dihydro-6h-pyrido eckige klammer auf 2,3-b eckige klammer zu eckige klammer auf 1,4 eckige klammer zu benzodiazepin-6- one, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| DE3204158A1 (de) * | 1982-02-06 | 1983-08-11 | Dr. Karl Thomae Gmbh, 7950 Biberach | "substituierte dibenzodiazepinone, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel" |
| DE3643666A1 (de) * | 1986-12-20 | 1988-06-30 | Thomae Gmbh Dr K | Neue kondensierte diazepinone, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| US5312819A (en) * | 1990-08-20 | 1994-05-17 | Sandoz Ltd. | Pharmaceutical compositions comprising clozapine and a radical scavenger |
| JP3749785B2 (ja) * | 1998-03-10 | 2006-03-01 | アース製薬株式会社 | 脱臭効力増強剤およびこれを用いた脱臭剤 |
| WO2012000528A1 (en) | 2010-07-01 | 2012-01-05 | Carl Zeiss Smt Gmbh | Optical system and multi facet mirror |
Family Cites Families (9)
| 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 | ||
| NL120551C (de) * | 1959-09-22 | |||
| CH438343A (de) * | 1962-11-08 | 1967-06-30 | Thomae Gmbh Dr K | Verfahren zur Herstellung von 5,6-Dihydro-6-oxo-11H-pyrido (2,3-b) (1,4)-benzodiazepinen |
| DE1238479B (de) * | 1964-01-28 | 1967-04-13 | Thomae Gmbh Dr K | Verfahren zur Herstellung von 5, 6-Dihydro-5-oxo-11H-pyrido-[2, 3-b] [1, 5]-benzodiazepinen |
| DE1251767B (de) * | 1964-02-28 | 1968-04-18 | Dr Karl Thomae Gesellschaft mit beschrankter Haftung Biberach/Riß | Verfahren zur Herstellung von neuen m 6 Stellung substituierten 5 6 Dihydro-5oxo HH pyrido[2,3-b] [l,5]benzodiazepinen |
| 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 |
| NL131929C (de) * | 1966-10-31 | |||
| 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. |
-
1970
- 1970-06-22 FI FI701744A patent/FI50242C/fi active
- 1970-06-25 SE SE7008854A patent/SE380800B/xx unknown
- 1970-07-09 CS CS4848A patent/CS164864B2/cs unknown
- 1970-07-13 US US54624A patent/US3691159A/en not_active Expired - Lifetime
- 1970-07-15 ZA ZA704861A patent/ZA704861B/xx unknown
- 1970-07-15 RO RO63923A patent/RO55559A/ro unknown
- 1970-07-15 CH CH1076270A patent/CH530988A/de not_active IP Right Cessation
- 1970-07-16 ES ES381898A patent/ES381898A1/es not_active Expired
- 1970-07-16 YU YU01810/70A patent/YU181070A/xx unknown
- 1970-07-16 BG BG015200A patent/BG17802A3/xx unknown
- 1970-07-17 FR FR7026501A patent/FR2059530B1/fr not_active Expired
- 1970-07-17 DK DK372570AA patent/DK135285B/da unknown
- 1970-07-17 BE BE753664D patent/BE753664A/xx unknown
- 1970-07-17 GB GB1265467D patent/GB1265467A/en not_active Expired
- 1970-07-17 IE IE933/70A patent/IE34393B1/xx unknown
- 1970-07-17 IL IL34947A patent/IL34947A/xx unknown
- 1970-07-17 AT AT654270A patent/AT298495B/de not_active IP Right Cessation
- 1970-07-17 NL NL7010618.A patent/NL165933C/xx not_active IP Right Cessation
- 1970-07-17 NO NO02815/70A patent/NO127447B/no unknown
- 1970-07-18 PL PL1970142155A patent/PL79758B1/pl unknown
-
1972
- 1972-08-01 US US00277096A patent/US3749785A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| PL79758B1 (en) | 1975-06-30 |
| IE34393B1 (en) | 1975-04-30 |
| NL165933C (nl) | 1981-06-15 |
| BG17802A3 (bg) | 1973-12-25 |
| GB1265467A (de) | 1972-03-01 |
| DK135285B (da) | 1977-03-28 |
| ES381898A1 (es) | 1973-04-01 |
| NL7010618A (de) | 1971-01-20 |
| YU181070A (en) | 1978-10-31 |
| IE34393L (en) | 1971-01-18 |
| IL34947A0 (en) | 1970-09-17 |
| CH530988A (de) | 1972-11-30 |
| FR2059530B1 (de) | 1974-08-30 |
| US3749785A (en) | 1973-07-31 |
| YU34241B (de) | 1979-04-30 |
| FR2059530A1 (de) | 1971-06-04 |
| US3691159A (en) | 1972-09-12 |
| RO55559A (de) | 1973-11-20 |
| SE380800B (sv) | 1975-11-17 |
| FI50242B (de) | 1975-09-30 |
| BE753664A (fr) | 1971-01-18 |
| CS164864B2 (de) | 1975-11-28 |
| IL34947A (en) | 1973-11-28 |
| AT298495B (de) | 1972-05-10 |
| FI50242C (fi) | 1976-01-12 |
| ZA704861B (en) | 1972-03-29 |
| DK135285C (de) | 1977-09-05 |
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