DE1929910A1 - Benzodiazepin-Derivate - Google Patents

Benzodiazepin-Derivate

Info

Publication number: DE1929910A1
Authority: DE; Germany
Prior art keywords: hydrogen; alkyl; formula; dihydro; pyrimidinyl
Prior art date: 1968-06-12
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.): Pending

Application number

DE19691929910

Other languages

German (de)

English (en)

Inventor

Archer Giles Allan

Sternbach Leo Henryk

Fryer Rodney Ian

Felix Arthur Martin

Arthur Stempel

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.)

F Hoffmann La Roche AG

Original Assignee

F Hoffmann La Roche AG

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.)

1968-06-12

Filing date

1969-06-12

Publication date

1970-01-02

1969-06-12 Application filed by F Hoffmann La Roche AG filed Critical F Hoffmann La Roche AG

1970-01-02 Publication of DE1929910A1 publication Critical patent/DE1929910A1/de

Status Pending legal-status Critical Current

Links

229940053197 benzodiazepine derivative antiepileptics Drugs 0.000 title claims description 8
125000003310 benzodiazepinyl group Chemical class N1N=C(C=CC2=C1C=CC=C2)* 0.000 title 1
150000001875 compounds Chemical class 0.000 claims description 78
239000001257 hydrogen Substances 0.000 claims description 58
229910052739 hydrogen Inorganic materials 0.000 claims description 58
125000000217 alkyl group Chemical group 0.000 claims description 43
-1 nitro, amino Chemical group 0.000 claims description 30
150000002431 hydrogen Chemical class 0.000 claims description 28
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 27
238000002360 preparation method Methods 0.000 claims description 25
238000000034 method Methods 0.000 claims description 23
150000003839 salts Chemical class 0.000 claims description 18
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 17
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 17
229910052736 halogen Inorganic materials 0.000 claims description 17
150000002367 halogens Chemical class 0.000 claims description 17
125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 17
239000002253 acid Substances 0.000 claims description 16
125000003545 alkoxy group Chemical group 0.000 claims description 15
239000000126 substance Substances 0.000 claims description 12
125000003282 alkyl amino group Chemical group 0.000 claims description 11
125000000753 cycloalkyl group Chemical group 0.000 claims description 10
150000001557 benzodiazepines Chemical class 0.000 claims description 8
238000004519 manufacturing process Methods 0.000 claims description 8
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 8
229940049706 benzodiazepine Drugs 0.000 claims description 7
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 7
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
229910052757 nitrogen Inorganic materials 0.000 claims description 7
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
229910001927 ruthenium tetroxide Inorganic materials 0.000 claims description 7
239000007787 solid Substances 0.000 claims description 7
125000001188 haloalkyl group Chemical group 0.000 claims description 6
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 5
150000001350 alkyl halides Chemical class 0.000 claims description 5
125000004414 alkyl thio group Chemical group 0.000 claims description 5
125000003277 amino group Chemical group 0.000 claims description 5
125000004103 aminoalkyl group Chemical group 0.000 claims description 5
229910021529 ammonia Inorganic materials 0.000 claims description 5
125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 5
125000000623 heterocyclic group Chemical group 0.000 claims description 5
229910052740 iodine Inorganic materials 0.000 claims description 5
125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
239000000825 pharmaceutical preparation Substances 0.000 claims description 5
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
RGGLEJFUEMKQSH-UHFFFAOYSA-N 1,4-benzodiazepin-2-one Chemical compound O=C1C=NC=C2C=CC=CC2=N1 RGGLEJFUEMKQSH-UHFFFAOYSA-N 0.000 claims description 3
CLUHZXYQKUXOOL-UHFFFAOYSA-N 1-methyl-7-nitro-5-pyrimidin-2-yl-2,3-dihydro-1,4-benzodiazepine Chemical compound C12=CC([N+]([O-])=O)=CC=C2N(C)CCN=C1C1=NC=CC=N1 CLUHZXYQKUXOOL-UHFFFAOYSA-N 0.000 claims description 3
238000000297 Sandmeyer reaction Methods 0.000 claims description 3
241001061127 Thione Species 0.000 claims description 3
125000004423 acyloxy group Chemical group 0.000 claims description 3
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
150000008050 dialkyl sulfates Chemical class 0.000 claims description 3
125000000714 pyrimidinyl group Chemical group 0.000 claims description 3
239000003795 chemical substances by application Substances 0.000 claims description 2
125000004663 dialkyl amino group Chemical group 0.000 claims description 2
239000012458 free base Substances 0.000 claims description 2
239000007788 liquid Substances 0.000 claims description 2
125000004356 hydroxy functional group Chemical group O* 0.000 claims 7
125000002252 acyl group Chemical group 0.000 claims 4
LRANPJDWHYRCER-UHFFFAOYSA-N 1,2-diazepine Chemical compound N1C=CC=CC=N1 LRANPJDWHYRCER-UHFFFAOYSA-N 0.000 claims 1
DEBLVPJOLMXEAW-UHFFFAOYSA-N 7-chloro-1,4-benzodiazepin-2-one Chemical compound O=C1C=NC=C2C=C(Cl)C=CC2=N1 DEBLVPJOLMXEAW-UHFFFAOYSA-N 0.000 claims 1
MGPDXXHYUGWQSW-UHFFFAOYSA-N 7-chloro-1-methyl-5-pyrimidin-2-yl-2,3-dihydro-1,4-benzodiazepine Chemical compound C12=CC(Cl)=CC=C2N(C)CCN=C1C1=NC=CC=N1 MGPDXXHYUGWQSW-UHFFFAOYSA-N 0.000 claims 1
239000004480 active ingredient Substances 0.000 claims 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
239000000969 carrier Substances 0.000 claims 1
231100000252 nontoxic Toxicity 0.000 claims 1
230000003000 nontoxic effect Effects 0.000 claims 1
239000000546 pharmaceutical excipient Substances 0.000 claims 1
230000001225 therapeutic effect Effects 0.000 claims 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 69
239000000243 solution Substances 0.000 description 48
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 43
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 42
238000002844 melting Methods 0.000 description 41
230000008018 melting Effects 0.000 description 41
239000000203 mixture Substances 0.000 description 38
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 30
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 25
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
241001465754 Metazoa Species 0.000 description 22
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
239000000047 product Substances 0.000 description 20
238000012360 testing method Methods 0.000 description 19
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
238000002425 crystallisation Methods 0.000 description 18
230000008025 crystallization Effects 0.000 description 18
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
241000699670 Mus sp. Species 0.000 description 12
230000000694 effects Effects 0.000 description 12
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
238000006243 chemical reaction Methods 0.000 description 11
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
238000001914 filtration Methods 0.000 description 10
230000007935 neutral effect Effects 0.000 description 10
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 10
239000011541 reaction mixture Substances 0.000 description 10
238000003756 stirring Methods 0.000 description 10
239000000725 suspension Substances 0.000 description 10
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 9
238000001816 cooling Methods 0.000 description 9
FZERHIULMFGESH-UHFFFAOYSA-N methylenecarboxanilide Natural products CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 description 9
239000003921 oil Substances 0.000 description 9
235000019198 oils Nutrition 0.000 description 9
239000002904 solvent Substances 0.000 description 9
206010010904 Convulsion Diseases 0.000 description 8
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
229910052938 sodium sulfate Inorganic materials 0.000 description 8
235000011152 sodium sulphate Nutrition 0.000 description 8
239000000460 chlorine Substances 0.000 description 7
238000000746 purification Methods 0.000 description 7
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 6
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
238000004821 distillation Methods 0.000 description 6
238000002474 experimental method Methods 0.000 description 6
238000000605 extraction Methods 0.000 description 6
239000000463 material Substances 0.000 description 6
239000000829 suppository Substances 0.000 description 6
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
229960001413 acetanilide Drugs 0.000 description 5
229960000583 acetic acid Drugs 0.000 description 5
239000012043 crude product Substances 0.000 description 5
239000013078 crystal Substances 0.000 description 5
239000000284 extract Substances 0.000 description 5
239000000706 filtrate Substances 0.000 description 5
239000012074 organic phase Substances 0.000 description 5
238000010992 reflux Methods 0.000 description 5
MEXNZUOOCNBUJU-UHFFFAOYSA-N (2-chlorophenyl)-pyrimidin-2-ylmethanone Chemical compound ClC1=CC=CC=C1C(=O)C1=NC=CC=N1 MEXNZUOOCNBUJU-UHFFFAOYSA-N 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
241000282326 Felis catus Species 0.000 description 4
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
241000607479 Yersinia pestis Species 0.000 description 4
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
238000009835 boiling Methods 0.000 description 4
239000002775 capsule Substances 0.000 description 4
239000003054 catalyst Substances 0.000 description 4
229910052801 chlorine Inorganic materials 0.000 description 4
238000001704 evaporation Methods 0.000 description 4
210000002683 foot Anatomy 0.000 description 4
239000012362 glacial acetic acid Substances 0.000 description 4
238000002347 injection Methods 0.000 description 4
239000007924 injection Substances 0.000 description 4
230000003647 oxidation Effects 0.000 description 4
238000007254 oxidation reaction Methods 0.000 description 4
WOCIAKWEIIZHES-UHFFFAOYSA-N ruthenium(iv) oxide Chemical compound O=[Ru]=O WOCIAKWEIIZHES-UHFFFAOYSA-N 0.000 description 4
229910000104 sodium hydride Inorganic materials 0.000 description 4
239000012312 sodium hydride Substances 0.000 description 4
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
GUJAGMICFDYKNR-UHFFFAOYSA-N 1,4-benzodiazepine Chemical class N1C=CN=CC2=CC=CC=C12 GUJAGMICFDYKNR-UHFFFAOYSA-N 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
241000699666 Mus <mouse, genus> Species 0.000 description 3
208000005392 Spasm Diseases 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 3
230000002378 acidificating effect Effects 0.000 description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
229910052794 bromium Inorganic materials 0.000 description 3
KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 3
SPWVRYZQLGQKGK-UHFFFAOYSA-N dichloromethane;hexane Chemical compound ClCCl.CCCCCC SPWVRYZQLGQKGK-UHFFFAOYSA-N 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 3
239000000499 gel Substances 0.000 description 3
210000000548 hind-foot Anatomy 0.000 description 3
150000002430 hydrocarbons Chemical group 0.000 description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
239000002480 mineral oil Substances 0.000 description 3
235000010446 mineral oil Nutrition 0.000 description 3
230000001624 sedative effect Effects 0.000 description 3
125000001424 substituent group Chemical group 0.000 description 3
TYRGAVXBIPMIGQ-UHFFFAOYSA-N (2-amino-5-chlorophenyl)-pyrimidin-2-ylmethanone Chemical compound NC1=CC=C(Cl)C=C1C(=O)C1=NC=CC=N1 TYRGAVXBIPMIGQ-UHFFFAOYSA-N 0.000 description 2
SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 description 2
BQZBKGGPTRPZBA-UHFFFAOYSA-N 7-chloro-1-methyl-5-pyrimidin-2-yl-3h-1,4-benzodiazepin-2-one Chemical compound N=1CC(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=NC=CC=N1 BQZBKGGPTRPZBA-UHFFFAOYSA-N 0.000 description 2
BSFOWENCYDHTPW-UHFFFAOYSA-N 7-nitro-5-pyrimidin-2-yl-2,3-dihydro-1h-1,4-benzodiazepine Chemical compound C12=CC([N+](=O)[O-])=CC=C2NCCN=C1C1=NC=CC=N1 BSFOWENCYDHTPW-UHFFFAOYSA-N 0.000 description 2
239000005711 Benzoic acid Substances 0.000 description 2
229910021591 Copper(I) chloride Inorganic materials 0.000 description 2
229920002261 Corn starch Polymers 0.000 description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
239000003810 Jones reagent Substances 0.000 description 2
241000124008 Mammalia Species 0.000 description 2
208000007101 Muscle Cramp Diseases 0.000 description 2
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
206010033799 Paralysis Diseases 0.000 description 2
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
229910000564 Raney nickel Inorganic materials 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
230000001773 anti-convulsant effect Effects 0.000 description 2
230000002082 anti-convulsion Effects 0.000 description 2
230000001754 anti-pyretic effect Effects 0.000 description 2
239000001961 anticonvulsive agent Substances 0.000 description 2
229960003965 antiepileptics Drugs 0.000 description 2
239000002585 base Substances 0.000 description 2
SLUNEGLMXGHOLY-UHFFFAOYSA-N benzene;hexane Chemical compound CCCCCC.C1=CC=CC=C1 SLUNEGLMXGHOLY-UHFFFAOYSA-N 0.000 description 2
235000010233 benzoic acid Nutrition 0.000 description 2
235000019445 benzyl alcohol Nutrition 0.000 description 2
125000001589 carboacyl group Chemical group 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
239000004203 carnauba wax Substances 0.000 description 2
235000013869 carnauba wax Nutrition 0.000 description 2
229940110456 cocoa butter Drugs 0.000 description 2
235000019868 cocoa butter Nutrition 0.000 description 2
OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 2
239000008120 corn starch Substances 0.000 description 2
229940099112 cornstarch Drugs 0.000 description 2
229940045803 cuprous chloride Drugs 0.000 description 2
239000011521 glass Substances 0.000 description 2
239000005457 ice water Substances 0.000 description 2
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
239000008101 lactose Substances 0.000 description 2
HCWCAKKEBCNQJP-UHFFFAOYSA-N magnesium orthosilicate Chemical compound [Mg+2].[Mg+2].[O-][Si]([O-])([O-])[O-] HCWCAKKEBCNQJP-UHFFFAOYSA-N 0.000 description 2
239000000391 magnesium silicate Substances 0.000 description 2
229910052919 magnesium silicate Inorganic materials 0.000 description 2
235000019792 magnesium silicate Nutrition 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
238000002156 mixing Methods 0.000 description 2
229910017604 nitric acid Inorganic materials 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
239000003208 petroleum Substances 0.000 description 2
239000012071 phase Substances 0.000 description 2
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 2
239000004299 sodium benzoate Substances 0.000 description 2
235000010234 sodium benzoate Nutrition 0.000 description 2
235000010288 sodium nitrite Nutrition 0.000 description 2
JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 2
239000007858 starting material Substances 0.000 description 2
208000024891 symptom Diseases 0.000 description 2
239000000454 talc Substances 0.000 description 2
229910052623 talc Inorganic materials 0.000 description 2
238000005303 weighing Methods 0.000 description 2
LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 1
ZAICQJHRVHLVEY-UHFFFAOYSA-N 2-(2-chlorophenyl)-2-pyrimidin-2-ylacetonitrile Chemical compound ClC1=CC=CC=C1C(C#N)C1=NC=CC=N1 ZAICQJHRVHLVEY-UHFFFAOYSA-N 0.000 description 1
LSTRKXWIZZZYAS-UHFFFAOYSA-N 2-bromoacetyl bromide Chemical compound BrCC(Br)=O LSTRKXWIZZZYAS-UHFFFAOYSA-N 0.000 description 1
125000003541 2-chlorobenzoyl group Chemical group ClC1=C(C(=O)*)C=CC=C1 0.000 description 1
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
UNCQVRBWJWWJBF-UHFFFAOYSA-N 2-chloropyrimidine Chemical compound ClC1=NC=CC=N1 UNCQVRBWJWWJBF-UHFFFAOYSA-N 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
244000215068 Acacia senegal Species 0.000 description 1
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
102100032219 Cathepsin D Human genes 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
229910021589 Copper(I) bromide Inorganic materials 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
229920000084 Gum arabic Polymers 0.000 description 1
101000869010 Homo sapiens Cathepsin D Proteins 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
CWRVKFFCRWGWCS-UHFFFAOYSA-N Pentrazole Chemical compound C1CCCCC2=NN=NN21 CWRVKFFCRWGWCS-UHFFFAOYSA-N 0.000 description 1
206010035148 Plague Diseases 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
239000007868 Raney catalyst Substances 0.000 description 1
241000700159 Rattus Species 0.000 description 1
240000004808 Saccharomyces cerevisiae Species 0.000 description 1
235000014680 Saccharomyces cerevisiae Nutrition 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
229910000831 Steel Inorganic materials 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
239000000205 acacia gum Substances 0.000 description 1
235000010489 acacia gum Nutrition 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
229910000102 alkali metal hydride Inorganic materials 0.000 description 1
150000008046 alkali metal hydrides Chemical class 0.000 description 1
125000002877 alkyl aryl group Chemical group 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
230000000049 anti-anxiety effect Effects 0.000 description 1
239000002249 anxiolytic agent Substances 0.000 description 1
239000008365 aqueous carrier Substances 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
ZVSBWXBFASGARJ-UHFFFAOYSA-N benzene;ethanol;hexane Chemical compound CCO.CCCCCC.C1=CC=CC=C1 ZVSBWXBFASGARJ-UHFFFAOYSA-N 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
230000037396 body weight Effects 0.000 description 1
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
235000011089 carbon dioxide Nutrition 0.000 description 1
239000012876 carrier material Substances 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
WBLIXGSTEMXDSM-UHFFFAOYSA-N chloromethane Chemical compound Cl[CH2] WBLIXGSTEMXDSM-UHFFFAOYSA-N 0.000 description 1
229940117975 chromium trioxide Drugs 0.000 description 1
GAMDZJFZMJECOS-UHFFFAOYSA-N chromium(6+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Cr+6] GAMDZJFZMJECOS-UHFFFAOYSA-N 0.000 description 1
238000004140 cleaning Methods 0.000 description 1
230000002566 clonic effect Effects 0.000 description 1
NKNDPYCGAZPOFS-UHFFFAOYSA-M copper(i) bromide Chemical compound Br[Cu] NKNDPYCGAZPOFS-UHFFFAOYSA-M 0.000 description 1
239000002178 crystalline material Substances 0.000 description 1
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
AVKAJIUWUFOCCN-UHFFFAOYSA-N dichloromethane;ethanol;hexane Chemical compound CCO.ClCCl.CCCCCC AVKAJIUWUFOCCN-UHFFFAOYSA-N 0.000 description 1
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
239000008298 dragée Substances 0.000 description 1
239000011363 dried mixture Substances 0.000 description 1
239000003814 drug Substances 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 1
NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
230000007717 exclusion Effects 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
239000006260 foam Substances 0.000 description 1
239000011888 foil Substances 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
229940093915 gynecological organic acid Drugs 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
125000003104 hexanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
229910000042 hydrogen bromide Inorganic materials 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
230000002757 inflammatory effect Effects 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
239000002198 insoluble material Substances 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
235000019359 magnesium stearate Nutrition 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
125000005905 mesyloxy group Chemical group 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
230000005012 migration Effects 0.000 description 1
238000013508 migration Methods 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
239000011812 mixed powder Substances 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
210000003205 muscle Anatomy 0.000 description 1
239000003158 myorelaxant agent Substances 0.000 description 1
PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
SUSQOBVLVYHIEX-UHFFFAOYSA-N o-phenylene-diaceto-nitrile Natural products N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
230000003204 osmotic effect Effects 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
HZAZVYAVYVKKCR-UHFFFAOYSA-N oxolane ruthenium Chemical compound [Ru].O1CCCC1 HZAZVYAVYVKKCR-UHFFFAOYSA-N 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
235000019271 petrolatum Nutrition 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 1
CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 1
229920001515 polyalkylene glycol Polymers 0.000 description 1
230000010181 polygamy Effects 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000003223 protective agent Substances 0.000 description 1
125000001453 quaternary ammonium group Chemical group 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
230000002040 relaxant effect Effects 0.000 description 1
230000002441 reversible effect Effects 0.000 description 1
230000000630 rising effect Effects 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000000932 sedative agent Substances 0.000 description 1
230000035939 shock Effects 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
239000002195 soluble material Substances 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000010959 steel Substances 0.000 description 1
230000001954 sterilising effect Effects 0.000 description 1
238000004659 sterilization and disinfection Methods 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
125000000547 substituted alkyl group Chemical group 0.000 description 1
239000003826 tablet Substances 0.000 description 1
235000012222 talc 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
238000004809 thin layer chromatography Methods 0.000 description 1
230000001256 tonic effect Effects 0.000 description 1
208000028325 tonic-clonic seizure Diseases 0.000 description 1
125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
239000003204 tranquilizing agent Substances 0.000 description 1
230000002936 tranquilizing effect Effects 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000008215 water for injection Substances 0.000 description 1
239000001993 wax Substances 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- 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
- A61K31/551—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole having two nitrogen atoms, e.g. dilazep
- A61K31/5513—1,4-Benzodiazepines, e.g. diazepam or clozapine
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/30—Halogen atoms or nitro radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/52—Two oxygen atoms
- C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/80—Inorganic fibres
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/82—Textiles which contain different kinds of fibres
- D06P3/854—Textiles which contain different kinds of fibres containing modified or unmodified fibres, i.e. containing the same type of fibres having different characteristics, e.g. twisted and not-twisted fibres

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Textile Engineering (AREA)
Health & Medical Sciences (AREA)
Inorganic Chemistry (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

DE19691929910 1968-06-12 1969-06-12 Benzodiazepin-Derivate Pending DE1929910A1 (de)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US73625068A	1968-06-12	1968-06-12
US80346169A	1969-02-28	1969-02-28

Publications (1)

Publication Number	Publication Date
DE1929910A1 true DE1929910A1 (de)	1970-01-02

Family

ID=27113017

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DE19691929910 Pending DE1929910A1 (de)	1968-06-12	1969-06-12	Benzodiazepin-Derivate

Country Status (12)

Country	Link
US (1)	US3546212A (xx)
AT (2)	AT289125B (xx)
BE (1)	BE734376A (xx)
CA (1)	CA950453A (xx)
CH (3)	CH550185A (xx)
DE (1)	DE1929910A1 (xx)
ES (1)	ES368239A1 (xx)
FR (1)	FR2010744A1 (xx)
GB (1)	GB1239380A (xx)
IE (1)	IE33286B1 (xx)
NL (3)	NL143927B (xx)
SE (1)	SE347510B (xx)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3836538A1 (de) *	1988-10-27	1990-05-03	Christian Rinke	Verpackungsbehaelter, insbesondere flasche
EP0410590A1 (en) *	1989-07-27	1991-01-30	AgrEvo UK Limited	Pyrimidinyl herbicides
EP0665224A4 (en) *	1992-10-16	1995-06-13	Nippon Soda Co	PYRIMIDINE DERIVATIVES.

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3723414A (en) *	1970-02-13	1973-03-27	Schering Corp	1-polyfluoroalkyl benzodiazepines
US3896109A (en) *	1971-09-30	1975-07-22	Upjohn Co	2,3-dehydro-1h-1,4-benzodiazepines
US4083948A (en) *	1977-04-04	1978-04-11	Hoffmann-La Roche, Inc.	Benzodiazepine radioimmunoassay using I125-label
SE7900456L (sv) *	1978-05-31	1979-07-20	Ferrosan As	Bensodiazeptinkoncentrationsbestemning
DE3124013A1 (de) *	1981-06-19	1982-12-30	Kali-Chemie Pharma Gmbh, 3000 Hannover	2-acylaminomethyl-1,4-benzodiazepin-verbindungen sowie verfahren und zwischenprodukte zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
DE3621551C1 (en) *	1986-06-27	1987-07-02	Eckard 5810 Witten De Feller	Cutting tool for lathe - has carrier arm and screw cooperating to retain lower packer plate and upper cutting insert in tool

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3371085A (en) *	1959-12-10	1968-02-27	Hoffmann La Roche	5-aryl-3h-1,4-benzodiazepin-2(1h)-ones

1968
- 1968-06-12 US US736250A patent/US3546212A/en not_active Expired - Lifetime
1969
- 1969-05-28 CH CH583472A patent/CH550185A/xx not_active IP Right Cessation
- 1969-05-28 CH CH806669A patent/CH523267A/de not_active IP Right Cessation
- 1969-06-06 CH CH872369A patent/CH523898A/de not_active IP Right Cessation
- 1969-06-06 NL NL696908658A patent/NL143927B/xx unknown
- 1969-06-10 SE SE08239/69A patent/SE347510B/xx unknown
- 1969-06-10 GB GB1239380D patent/GB1239380A/en not_active Expired
- 1969-06-11 BE BE734376D patent/BE734376A/xx unknown
- 1969-06-11 AT AT554069A patent/AT289125B/de not_active IP Right Cessation
- 1969-06-11 ES ES368239A patent/ES368239A1/es not_active Expired
- 1969-06-11 IE IE797/69A patent/IE33286B1/xx unknown
- 1969-06-11 AT AT167371A patent/AT299960B/de not_active IP Right Cessation
- 1969-06-11 NL NL6908866A patent/NL6908866A/xx unknown
- 1969-06-11 FR FR6919321A patent/FR2010744A1/fr not_active Withdrawn
- 1969-06-12 NL NL6908966A patent/NL6908966A/xx unknown
- 1969-06-12 DE DE19691929910 patent/DE1929910A1/de active Pending
- 1969-06-12 CA CA054,138,A patent/CA950453A/en not_active Expired

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3836538A1 (de) *	1988-10-27	1990-05-03	Christian Rinke	Verpackungsbehaelter, insbesondere flasche
EP0410590A1 (en) *	1989-07-27	1991-01-30	AgrEvo UK Limited	Pyrimidinyl herbicides
EP0665224A4 (en) *	1992-10-16	1995-06-13	Nippon Soda Co	PYRIMIDINE DERIVATIVES.
EP0665224A1 (en) *	1992-10-16	1995-08-02	Nippon Soda Co., Ltd.	Pyrimidine derivative

Also Published As

Publication number	Publication date
US3546212A (en)	1970-12-08
AT289125B (de)	1971-04-13
AT299960B (de)	1972-07-10
BE734376A (xx)	1969-12-11
IE33286L (en)	1969-12-12
NL143927B (nl)	1974-11-15
GB1239380A (xx)	1971-07-14
CA950453A (en)	1974-07-02
NL6908866A (xx)	1969-12-22
IE33286B1 (en)	1974-05-15
ES368239A1 (es)	1971-06-16
CH523898A (de)	1972-06-15
FR2010744A1 (xx)	1970-02-20
NL6908966A (xx)	1969-12-16
NL6908658A (xx)	1969-12-16
CH550185A (de)	1974-06-14
SE347510B (xx)	1972-08-07
CH523267A (de)	1972-05-31

Legal Events

Date	Code	Title	Description
1978-05-18	OHJ	Non-payment of the annual fee

Publication	Publication Date	Title
DE2012190C3 (de)	1980-11-13	l-Methyl-e-phenyl-e-chloMH-s- triazole- [43-a] [1,4] benzodiazepine, ein Verfahren zu ihrer Herstellung sowie diese enthaltende Arzneimittel
DE2005276C3 (de)	1978-08-31	6,7,8,9-Tetrahydro-5-phenyl -IH [1] benzothieno [23-e-] [1,4] diazepin-2(3-H)-on und dessen pharmazeutisch verträgliche Salze
DE2203782A1 (de)	1972-08-24	Verfahren zur Herstellung von Triazolobenzodiazepinen sowie neue Triazolobenzodiazepine und deren Zwischenprodukte
DD155988A5 (de)	1982-07-21	Verfahren zur herstellung von 2-acylaminomethyl-1,4-benzodiazepine und deren salze
DE1907670C3 (xx)	1981-01-29
DE1810423B2 (de)	1973-03-22	1-phenyl-4-alkyl-1,2,4,5-tetrahydro-3h-1,4-benzodiazepin-2,5-dionderivate
DE2321705A1 (de)	1973-11-15	Benzodiazepinderivate, ihre herstellung und verwendung
DE1929910A1 (de)	1970-01-02	Benzodiazepin-Derivate
CH622019A5 (en)	1981-03-13	Process for the preparation of aminotriazolobenzodiazepines
DE1770778A1 (de)	1972-02-17	Benzodiazepin-Derivate
DE1670305C3 (de)	1982-03-25	5-Phenyl-2,4-dioxo-1,2,3,4-tetrahydro-3H-1,5-benzodiazepine und Verfahren zu ihrer Herstellung
DE2055889C2 (de)	1982-04-01	2-Alkyl-s-triazolo [1,5-a] [1,4] benzodiazepinderivate, Verfahren zu ihrer Herstellung und sie enthaltende Arzneimittel
DE1668634B2 (xx)	1979-02-08
WO1996023790A1 (de)	1996-08-08	Acetylimidazobenzodiazepine
DE2807145A1 (de)	1978-08-31	Pyrrolochinoxalinone und pyrrolobenzdiazepinone, verfahren zu ihrer herstellung und ihre verwendung
DE2242059A1 (de)	1973-03-15	2,4-dihydro-1h-s-triazolo eckige klammer auf 4,3-a eckige klammer zu eckige klammer auf 1,4 eckige klammer zu benzodiazepine und verfahren zu ihrer herstellung
DE2002882A1 (de)	1970-08-13	Benzodiazepin-Derivate
DE2456311A1 (de)	1975-06-05	Benzodiazepinderivate
EP0072029B1 (de)	1986-10-22	Triazolobenzazepine, Verfahren und Zwischenprodukte zu deren Herstellung und diese enthaltende Arzneimittel
DE2259471C2 (de)	1982-08-19	2-Halogen-9-phenyl-5,6-dihydro-7H-pyrido [2,3-f] [1,4] diazepinderivate
DE2030669A1 (de)	1971-01-07	Benzodiazepin Derivate
DE2550163C2 (de)	1984-11-22	Neue Derivate des [1,4]Oxathiino[2,3-c]pyrrols, deren Herstellung und diese enthaltende Zusammensetzungen
DE2000775A1 (de)	1970-10-01	Substituierte 1,2,3,4-Tetrahydrobenzothieno-[2,3-c]-pyridinderivate und Verfahren zu deren Herstellung
DE2423642C2 (de)	1986-11-20	Substituierte 6,7,8,9-Tetrahydro-1H-pyrazolo[3,4-b][1,5]-diazocinverbindungen, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel
DE2223648A1 (de)	1972-11-16	Benzodiazepin-Derivate