DD275050A5 - Verfahren zur herstellung von 1,3,4,16b-tetrahydro-2h,10h-indde[2,1-c]-pyrazine [1,2-a][1,4]benzodiazepin-derivaten - Google Patents

Verfahren zur herstellung von 1,3,4,16b-tetrahydro-2h,10h-indde[2,1-c]-pyrazine [1,2-a][1,4]benzodiazepin-derivaten Download PDF

Info

Publication number: DD275050A5
Authority: DD; German Democratic Republic
Prior art keywords: hydrogen; compounds; lower alkyl; formula; group
Prior art date: 1986-10-01

Application number

DD87307377A

Other languages

German (de)

English (en)

Inventor

Jan W F Wasley

Original Assignee

��`��@��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.)

1986-10-01

Filing date

1987-09-29

Publication date

1990-01-10

1987-09-29 Application filed by ��`��@��k�� filed Critical ��`��@��k��

1990-01-10 Publication of DD275050A5 publication Critical patent/DD275050A5/de

Links

238000000034 method Methods 0.000 title claims abstract description 45
238000002360 preparation method Methods 0.000 title claims abstract description 20
230000008569 process Effects 0.000 title claims abstract description 17
GUJAGMICFDYKNR-UHFFFAOYSA-N 1,4-benzodiazepine Chemical class N1C=CN=CC2=CC=CC=C12 GUJAGMICFDYKNR-UHFFFAOYSA-N 0.000 title description 7
150000001875 compounds Chemical class 0.000 claims abstract description 158
125000001424 substituent group Chemical group 0.000 claims abstract description 34
125000004043 oxo group Chemical group O=* 0.000 claims abstract description 17
239000003638 chemical reducing agent Substances 0.000 claims abstract description 8
229910052739 hydrogen Inorganic materials 0.000 claims description 74
239000001257 hydrogen Substances 0.000 claims description 74
125000000217 alkyl group Chemical group 0.000 claims description 61
-1 hydroxy, amino Chemical group 0.000 claims description 59
150000003839 salts Chemical class 0.000 claims description 45
150000002431 hydrogen Chemical class 0.000 claims description 44
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 30
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 28
239000000243 solution Substances 0.000 claims description 28
229910052736 halogen Inorganic materials 0.000 claims description 25
150000002367 halogens Chemical class 0.000 claims description 25
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 25
125000003545 alkoxy group Chemical group 0.000 claims description 21
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 20
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 18
125000003282 alkyl amino group Chemical group 0.000 claims description 13
229910052799 carbon Inorganic materials 0.000 claims description 13
125000006239 protecting group Chemical group 0.000 claims description 13
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 13
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 12
125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 12
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 10
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
229920006395 saturated elastomer Polymers 0.000 claims description 10
125000004432 carbon atom Chemical group C* 0.000 claims description 8
125000003342 alkenyl group Chemical group 0.000 claims description 7
229910052757 nitrogen Inorganic materials 0.000 claims description 7
230000000269 nucleophilic effect Effects 0.000 claims description 6
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 5
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
125000004414 alkyl thio group Chemical group 0.000 claims description 4
125000000304 alkynyl group Chemical group 0.000 claims description 4
125000001589 carboacyl group Chemical group 0.000 claims description 4
239000003814 drug Substances 0.000 claims description 4
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 4
239000000546 pharmaceutical excipient Substances 0.000 claims description 4
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239000002775 capsule Substances 0.000 claims description 3
125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
239000011230 binding agent Substances 0.000 claims description 2
239000000314 lubricant Substances 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
239000000829 suppository Substances 0.000 claims description 2
PBTAYWARJQPTGM-UHFFFAOYSA-N 1h-1,4-benzodiazepin-2-ol Chemical compound N1C(O)=CN=CC2=CC=CC=C21 PBTAYWARJQPTGM-UHFFFAOYSA-N 0.000 claims 1
238000002347 injection Methods 0.000 claims 1
239000007924 injection Substances 0.000 claims 1
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
239000006187 pill Substances 0.000 claims 1
WPGUWABWNUSPMW-UHFFFAOYSA-N serazapine Chemical compound C1N2C3=CC=CC=C3C(C(=O)OC)=C2C2CN(C)CCN2C2=CC=CC=C21 WPGUWABWNUSPMW-UHFFFAOYSA-N 0.000 claims 1
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239000002464 receptor antagonist Substances 0.000 abstract description 5
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125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 abstract description 2
125000003310 benzodiazepinyl group Chemical class N1N=C(C=CC2=C1C=CC=C2)* 0.000 abstract 2
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 51
239000007858 starting material Substances 0.000 description 37
239000000203 mixture Substances 0.000 description 35
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
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238000006243 chemical reaction Methods 0.000 description 21
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239000002253 acid Substances 0.000 description 13
230000002829 reductive effect Effects 0.000 description 13
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YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 12
239000002585 base Substances 0.000 description 11
239000002904 solvent Substances 0.000 description 11
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 10
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CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
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238000000354 decomposition reaction Methods 0.000 description 9
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 9
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
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201000010099 disease Diseases 0.000 description 8
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238000012360 testing method Methods 0.000 description 7
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
239000004480 active ingredient Substances 0.000 description 6
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239000000706 filtrate Substances 0.000 description 6
125000000524 functional group Chemical group 0.000 description 6
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
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KVIOIFKWKBDGAV-UHFFFAOYSA-N 58881-41-7 Chemical compound C1=CC=C2N3C(=O)C4=CC5=CC=CC=C5N4C(=O)C3=CC2=C1 KVIOIFKWKBDGAV-UHFFFAOYSA-N 0.000 description 5
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
208000019901 Anxiety disease Diseases 0.000 description 5
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
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238000001727 in vivo Methods 0.000 description 5
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QXAUTQFAWKKNLM-UHFFFAOYSA-N methyl indole-3-carboxylate Chemical compound C1=CC=C2C(C(=O)OC)=CNC2=C1 QXAUTQFAWKKNLM-UHFFFAOYSA-N 0.000 description 5
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QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 4
VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 4
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
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125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
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239000012280 lithium aluminium hydride Substances 0.000 description 4
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UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
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YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 3
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AFRJJFRNGGLMDW-UHFFFAOYSA-N lithium amide Chemical compound [Li+].[NH2-] AFRJJFRNGGLMDW-UHFFFAOYSA-N 0.000 description 3
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235000020232 peanut Nutrition 0.000 description 1
229940021222 peritoneal dialysis isotonic solution Drugs 0.000 description 1
XCRBXWCUXJNEFX-UHFFFAOYSA-N peroxybenzoic acid Chemical class OOC(=O)C1=CC=CC=C1 XCRBXWCUXJNEFX-UHFFFAOYSA-N 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
238000003408 phase transfer catalysis Methods 0.000 description 1
WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
229920000768 polyamine Polymers 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
102000004196 processed proteins & peptides Human genes 0.000 description 1
108090000765 processed proteins & peptides Proteins 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000011241 protective layer Substances 0.000 description 1
230000000506 psychotropic effect Effects 0.000 description 1
NKTROCRBBTZUPL-UHFFFAOYSA-N pyrazino[1,2-a][1,4]benzodiazepine Chemical compound N1=CC2=CC=CC=C2N2C=CN=CC2=C1 NKTROCRBBTZUPL-UHFFFAOYSA-N 0.000 description 1
229960000948 quinine Drugs 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
238000001525 receptor binding assay Methods 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000005932 reductive alkylation reaction Methods 0.000 description 1
238000007788 roughening Methods 0.000 description 1
230000007017 scission Effects 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
230000036280 sedation Effects 0.000 description 1
239000003215 serotonin 5-HT2 receptor antagonist Substances 0.000 description 1
229940121356 serotonin receptor antagonist Drugs 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
239000002002 slurry Substances 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
KOUDKOMXLMXFKX-UHFFFAOYSA-N sodium oxido(oxo)phosphanium hydrate Chemical compound O.[Na+].[O-][PH+]=O KOUDKOMXLMXFKX-UHFFFAOYSA-N 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
238000003797 solvolysis reaction Methods 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
241000894007 species Species 0.000 description 1
208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
238000011699 spontaneously hypertensive rat Methods 0.000 description 1
238000013222 sprague-dawley male rat Methods 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
QMGVPVSNSZLJIA-FVWCLLPLSA-N strychnine Chemical class O([C@H]1CC(N([C@H]2[C@H]1[C@H]1C3)C=4C5=CC=CC=4)=O)CC=C1CN1[C@@H]3[C@]25CC1 QMGVPVSNSZLJIA-FVWCLLPLSA-N 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
235000010983 sucrose acetate isobutyrate Nutrition 0.000 description 1
UVGUPMLLGBCFEJ-SWTLDUCYSA-N sucrose acetate isobutyrate Chemical compound CC(C)C(=O)O[C@H]1[C@H](OC(=O)C(C)C)[C@@H](COC(=O)C(C)C)O[C@@]1(COC(C)=O)O[C@@H]1[C@H](OC(=O)C(C)C)[C@@H](OC(=O)C(C)C)[C@H](OC(=O)C(C)C)[C@@H](COC(C)=O)O1 UVGUPMLLGBCFEJ-SWTLDUCYSA-N 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
150000003899 tartaric acid esters Chemical class 0.000 description 1
125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
230000009466 transformation Effects 0.000 description 1
PVFOMCVHYWHZJE-UHFFFAOYSA-N trichloroacetyl chloride Chemical compound ClC(=O)C(Cl)(Cl)Cl PVFOMCVHYWHZJE-UHFFFAOYSA-N 0.000 description 1
230000002792 vascular Effects 0.000 description 1
230000007279 water homeostasis Effects 0.000 description 1
238000009736 wetting Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- 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
- C07D487/12—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 three hetero rings
- C07D487/14—Ortho-condensed systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Life Sciences & Earth Sciences (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)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

DD87307377A 1986-10-01 1987-09-29 Verfahren zur herstellung von 1,3,4,16b-tetrahydro-2h,10h-indde[2,1-c]-pyrazine [1,2-a][1,4]benzodiazepin-derivaten DD275050A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US06/914,028 US4737496A (en)	1986-10-01	1986-10-01	1,3,4,16b-tetrahydro-2H,10H-indolo[2,1-c]pyrazino-[1,2-a][1,4]benzodiazepines useful as serotonin-2 receptor antagonists

Publications (1)

Publication Number	Publication Date
DD275050A5 true DD275050A5 (de)	1990-01-10

Family

ID=25433828

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD87307377A DD275050A5 (de)	1986-10-01	1987-09-29	Verfahren zur herstellung von 1,3,4,16b-tetrahydro-2h,10h-indde[2,1-c]-pyrazine [1,2-a][1,4]benzodiazepin-derivaten

Country Status (19)

Country	Link
US (1)	US4737496A (pt)
EP (1)	EP0266308B1 (pt)
JP (1)	JPS6396187A (pt)
KR (1)	KR880005134A (pt)
AT (1)	ATE65503T1 (pt)
AU (1)	AU605507B2 (pt)
DD (1)	DD275050A5 (pt)
DE (1)	DE3771652D1 (pt)
DK (1)	DK513087A (pt)
ES (1)	ES2044971T3 (pt)
FI (1)	FI874245A7 (pt)
GR (1)	GR3002362T3 (pt)
HU (1)	HU198937B (pt)
IL (1)	IL84009A (pt)
NO (1)	NO166186C (pt)
NZ (1)	NZ221975A (pt)
PH (1)	PH24754A (pt)
PT (1)	PT85822B (pt)
ZA (1)	ZA877360B (pt)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3803620A1 (de) *	1988-02-06	1989-08-17	Goedecke Ag	Indolocarbazol-derivate, verfahren zu deren herstellung und diese enthaltende arzneimittel
US4897392A (en) *	1989-07-03	1990-01-30	Hoechst-Roussel Pharmaceuticals, Inc.	4H-indolo(1,2-d)(1,2,4)triazolo(4,3-A)(1,4)benzodiazepines
WO2009082268A2 (ru)	2007-12-21	2009-07-02	Alla Chem, Llc	ЛИГАНДЫ α-АДРЕНОЦЕПТОРОВ, ДОПАМИНОВЫХ, ГИСТАМИНОВЫХ, ИМИДАЗОЛИНОВЫХ И СЕРОТОНИНОВЫХ РЕЦЕПТОРОВ И ИХ ПРИМЕНЕНИЕ
CN103288831A (zh) *	2012-02-24	2013-09-11	中国科学院大连化学物理研究所	一种合成手性二氢-6H-吲哚并[2,1-c][1,4]-苯并二氮杂卓-6-酮的方法
CN103288830A (zh) *	2012-02-24	2013-09-11	中国科学院大连化学物理研究所	一种合成手性二氢-5H-吡咯并[2,1-c][1,4]-苯并二氮杂卓的方法
CN103288828A (zh) *	2012-02-24	2013-09-11	中国科学院大连化学物理研究所	一种合成手性二氢-6H-吲哚并[2,1-c][1,4]-苯并二氮杂卓的方法
CN110437236B (zh) *	2019-08-28	2020-08-18	青岛农业大学	一种吲哚-1,2-并1,4-苯并二氮杂卓类化合物及其合成方法

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4316900A (en) *	1977-10-05	1982-02-23	Ciba-Geigy Corporation	Piperazinopyrrolobenzodiazepines
ZA784475B (en) *	1977-10-05	1979-07-25	Ciba Geigy Ag	Piperazinopyrrolobenzodiazepines
US4192803A (en) *	1978-09-15	1980-03-11	American Cyanamid Company	5H-Pyrrolo[2,1-c][1,4]benzodiazepine derivatives
US4362666A (en) *	1979-08-22	1982-12-07	Ciba-Geigy Corporation	Diazepinopyrrolobenzodiazepines
US4424221A (en) *	1982-09-28	1984-01-03	Ciba-Geigy Corporation	Method of treating anxiety
US4529724A (en) *	1983-10-11	1985-07-16	Mcneilab, Inc.	6H-indolo[2,1-c][1,4]benzodiazepines and 12-oxo derivatives useful as antihypertensives
US4587244A (en) *	1984-04-11	1986-05-06	Mcneilab, Inc.	Amidine benzodiazepines, methods for their use and intermediates
US4547497A (en) *	1984-04-11	1985-10-15	Mcneilab, Inc.	Amidine benzodiazepines, methods for their use and intermediates
US4596799A (en) *	1985-01-29	1986-06-24	Ciba-Geigy Corporation	9H-pyrrolo[2,1-c]-1,2,4-triazolo[4,3-a][1,4]benzodiazepines

1986
- 1986-10-01 US US06/914,028 patent/US4737496A/en not_active Expired - Fee Related
1987
- 1987-09-03 PH PH35768A patent/PH24754A/en unknown
- 1987-09-25 DE DE8787810557T patent/DE3771652D1/de not_active Expired - Lifetime
- 1987-09-25 EP EP87810557A patent/EP0266308B1/de not_active Expired - Lifetime
- 1987-09-25 ES ES87810557T patent/ES2044971T3/es not_active Expired - Lifetime
- 1987-09-25 AT AT87810557T patent/ATE65503T1/de not_active IP Right Cessation
- 1987-09-28 FI FI874245A patent/FI874245A7/fi not_active Application Discontinuation
- 1987-09-28 IL IL84009A patent/IL84009A/xx not_active IP Right Cessation
- 1987-09-29 NZ NZ221975A patent/NZ221975A/xx unknown
- 1987-09-29 PT PT85822A patent/PT85822B/pt not_active IP Right Cessation
- 1987-09-29 DK DK513087A patent/DK513087A/da not_active Application Discontinuation
- 1987-09-29 DD DD87307377A patent/DD275050A5/de not_active IP Right Cessation
- 1987-09-30 KR KR870010880A patent/KR880005134A/ko not_active Withdrawn
- 1987-09-30 JP JP62244425A patent/JPS6396187A/ja active Pending
- 1987-09-30 NO NO874111A patent/NO166186C/no unknown
- 1987-09-30 ZA ZA877360A patent/ZA877360B/xx unknown
- 1987-09-30 AU AU79094/87A patent/AU605507B2/en not_active Ceased
- 1987-09-30 HU HU874415A patent/HU198937B/hu not_active IP Right Cessation
1991
- 1991-07-25 GR GR91400909T patent/GR3002362T3/el unknown

Also Published As

Publication number	Publication date
IL84009A (en)	1992-01-15
US4737496A (en)	1988-04-12
ES2044971T3 (es)	1994-01-16
JPS6396187A (ja)	1988-04-27
AU605507B2 (en)	1991-01-17
IL84009A0 (en)	1988-02-29
NO166186C (no)	1991-06-12
GR3002362T3 (en)	1992-12-30
DK513087D0 (da)	1987-09-29
PH24754A (en)	1990-10-01
AU7909487A (en)	1988-04-14
EP0266308A1 (de)	1988-05-04
FI874245A0 (fi)	1987-09-28
ATE65503T1 (de)	1991-08-15
NO874111D0 (no)	1987-09-30
DK513087A (da)	1988-04-02
EP0266308B1 (de)	1991-07-24
HUT47284A (en)	1989-02-28
NO166186B (no)	1991-03-04
DE3771652D1 (de)	1991-08-29
FI874245A7 (fi)	1988-04-02
ZA877360B (en)	1989-06-28
KR880005134A (ko)	1988-06-28
HU198937B (en)	1989-12-28
PT85822B (pt)	1990-07-31
PT85822A (pt)	1987-10-01
NZ221975A (en)	1990-02-26
NO874111L (no)	1988-04-05

Legal Events

Date	Code	Title	Description
1995-06-22	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
DE2901181C2 (de)	1984-07-19	N-(1-Alkyl- bzw. Allyl-2-pyrrolidinylmethyl)-2-methoxy-4-amino-5-alkylsulfonylbenzamide, deren Salze, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel
DE69325199T2 (de)	1999-12-16	Triazolopyridazine als Antiasthmatika
DD273833A5 (de)	1989-11-29	N 9 - cyclopentylsubstituierte adeninderivate
DE60309057T2 (de)	2007-04-12	Azabicycloderivate als antagonisten des muscarinischen rezeptors
DD227963A5 (de)	1985-10-02	Verfahren zur herstellung von 1-benzyl-aminoalkyl-pyrrolidinone
CH621115A5 (pt)	1981-01-15
DE2924681A1 (de)	1980-01-10	Phenylpiperazinderivate, verfahren zu ihrer herstellung und sie enthaltende arzneimittel
WO1997032865A1 (de)	1997-09-12	Neue arylglycinamidderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende pharmazeutische zusammensetzungen
EP0000220B1 (de)	1981-04-29	Dihydrouracile, Verfahren zu ihrer Herstellung und sie enthaltende Arzneimittel
DE2851028A1 (de)	1979-05-31	Neue indolo eckige klammer auf 2.3-a eckige klammer zu chinolizidine, verfahren zu ihrer herstellung und sie enthaltende pharmazeutische zubereitung
DE3149010A1 (de)	1983-07-07	(+)-2-(1-(2,6-dichlorphenoxy)-ethyl)-1,3- diazacyclopent-2-en, dessen herstellung und seine verwendung in pharamazeutischen praeparaten
DD235256A5 (de)	1986-04-30	Verfahren zur herstellung neuer substituierter pyrrolidinone
DE69308115T2 (de)	1997-05-28	(-)-ritodrin
DE19824470A1 (de)	1999-12-02	Neue Neurokininantagonisten, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende pharmazeutische Zusammensetzungen
DD275050A5 (de)	1990-01-10	Verfahren zur herstellung von 1,3,4,16b-tetrahydro-2h,10h-indde[2,1-c]-pyrazine [1,2-a][1,4]benzodiazepin-derivaten
CH520680A (de)	1972-03-31	Verfahren zur Herstellung neuer Mutterkornpeptidalkaloide
DE69411616T2 (de)	1998-11-19	Triazolopyridazin-Derivate, ihre Herstellung und Verwendung
DE2362754C2 (de)	1985-11-21	Cyclopropylalkylaminoreste enthaltende Oxazolinverbindungen, Verfahren zu deren Herstellung und diese Verbindungen enthaltende Arzneimittel
DE2719294A1 (de)	1977-11-17	Neue derivate des 1,4-benzodioxans, verfahren zu deren herstellung und diese enthaltende pharmazeutische zusammensetzungen
DD282457A5 (de)	1990-09-12	Verfahren zur herstellung neuer heterocyclischer derivate
DE68905363T2 (de)	1993-08-05	Heterotetracyclische laktamderivate, verfahren zu ihrer herstellung und pharmazeutische zubereitungen, die sie enthalten.
EP0389425B1 (de)	1995-04-26	Neue Benzothiopyranylamine
DE2305514A1 (de)	1973-08-16	Verfahren zur herstellung von lysergsaeureamiden und dihydrolysergsaeureamiden sowie lysergsaeureamide und dihydrolysergsaeureamide und ihre verwendung
DE3320028A1 (de)	1983-12-08	8-amino-4-phenyl-2-methyl-1,2,3,4-tetrahydro-isochinolinderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
DE69104155T2 (de)	1995-05-04	6-Alkylpyridazinderivate, Verfahren zu deren Herstellung und diese enthaltende Zusammensetzungen.