HRP931082A2 - Pyridoindolobenzodiazepines and derivatives as antipsychotics - Google Patents
Pyridoindolobenzodiazepines and derivatives as antipsychotics Download PDFInfo
- Publication number
- HRP931082A2 HRP931082A2 HR07/921,051A HRP931082A HRP931082A2 HR P931082 A2 HRP931082 A2 HR P931082A2 HR P931082 A HRP931082 A HR P931082A HR P931082 A2 HRP931082 A2 HR P931082A2
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- Prior art keywords
- carbon atoms
- alkyl
- compound
- cycloalkyl
- effective amount
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- 239000000164 antipsychotic agent Substances 0.000 title description 8
- 229940005529 antipsychotics Drugs 0.000 title description 6
- FBIQIXOGUZLOAN-UHFFFAOYSA-N C1=CN=NC2=C3C(C=CC4=NC=CC=C44)=C4N=C3C=CC2=C1 Chemical class C1=CN=NC2=C3C(C=CC4=NC=CC=C44)=C4N=C3C=CC2=C1 FBIQIXOGUZLOAN-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 88
- 125000004432 carbon atom Chemical group C* 0.000 claims description 60
- 125000000217 alkyl group Chemical group 0.000 claims description 47
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 17
- 150000003839 salts Chemical class 0.000 claims description 14
- 229910052760 oxygen Inorganic materials 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 229910052801 chlorine Inorganic materials 0.000 claims description 10
- 229910052731 fluorine Inorganic materials 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 9
- 208000011963 Substance-induced psychotic disease Diseases 0.000 claims description 8
- 231100000393 Substance-induced psychotic disorder Toxicity 0.000 claims description 8
- 230000000561 anti-psychotic effect Effects 0.000 claims description 8
- 201000002545 drug psychosis Diseases 0.000 claims description 8
- 208000009985 drug-induced dyskinesia Diseases 0.000 claims description 8
- 230000003374 anti-dyskinetic effect Effects 0.000 claims description 7
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 7
- 229940049706 benzodiazepine Drugs 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 125000001072 heteroaryl group Chemical group 0.000 claims description 6
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims description 3
- -1 CH2H5O Chemical group 0.000 claims description 3
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 3
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- SJQMPGVCBUUGAL-UHFFFAOYSA-N 17-fluoro-5,10,14-trimethyl-1,5,14-triazapentacyclo[10.8.1.02,7.08,21.015,20]henicosa-2(7),8,10,12(21),15(20),16,18-heptaene Chemical compound C1=2C3=CC(C)=CC=2CN(C)C2=CC(F)=CC=C2N1C1=C3CN(C)CC1 SJQMPGVCBUUGAL-UHFFFAOYSA-N 0.000 claims description 2
- YELHOTUHGZRBAR-UHFFFAOYSA-N 5-(cyclohexylmethyl)-17-(trifluoromethyl)-1,5,14-triazapentacyclo[10.8.1.02,7.08,21.015,20]henicosa-2(7),8,10,12(21),15(20),16,18-heptaene Chemical compound C=1C(C(F)(F)F)=CC=C(N(C=2CC3)C4=5)C=1NCC4=CC=CC=5C=2CN3CC1CCCCC1 YELHOTUHGZRBAR-UHFFFAOYSA-N 0.000 claims description 2
- MQQHKPFTZVIHOV-UHFFFAOYSA-N 5-benzyl-17-chloro-1,5,14-triazapentacyclo[10.8.1.02,7.08,21.015,20]henicosa-2(7),8,10,12(21),15(20),16,18-heptaene Chemical compound C=1C(Cl)=CC=C(N(C=2CC3)C4=5)C=1NCC4=CC=CC=5C=2CN3CC1=CC=CC=C1 MQQHKPFTZVIHOV-UHFFFAOYSA-N 0.000 claims description 2
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- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 150000008038 benzoazepines Chemical class 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 description 1
- 125000002618 bicyclic heterocycle group Chemical group 0.000 description 1
- 150000001602 bicycloalkyls Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 229910000085 borane Inorganic materials 0.000 description 1
- 238000009395 breeding Methods 0.000 description 1
- 230000001488 breeding effect Effects 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- FFSAXUULYPJSKH-UHFFFAOYSA-N butyrophenone Chemical class CCCC(=O)C1=CC=CC=C1 FFSAXUULYPJSKH-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 235000010980 cellulose Nutrition 0.000 description 1
- 239000003874 central nervous system depressant Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- ZPEIMTDSQAKGNT-UHFFFAOYSA-N chlorpromazine Chemical compound C1=C(Cl)C=C2N(CCCN(C)C)C3=CC=CC=C3SC2=C1 ZPEIMTDSQAKGNT-UHFFFAOYSA-N 0.000 description 1
- 229960001076 chlorpromazine Drugs 0.000 description 1
- 238000013270 controlled release Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- XSYZCZPCBXYQTE-UHFFFAOYSA-N cyclodecylcyclodecane Chemical compound C1CCCCCCCCC1C1CCCCCCCCC1 XSYZCZPCBXYQTE-UHFFFAOYSA-N 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([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
- 125000004856 decahydroquinolinyl group Chemical group N1(CCCC2CCCCC12)* 0.000 description 1
- 239000002027 dichloromethane extract Substances 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000003255 drug test Methods 0.000 description 1
- 230000000142 dyskinetic effect Effects 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 150000004820 halides Chemical group 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 229960003878 haloperidol Drugs 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 1
- 125000004926 indolenyl group Chemical group 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 239000003041 laboratory chemical Substances 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
- 229960002216 methylparaben Drugs 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 125000004930 octahydroisoquinolinyl group Chemical group C1(NCCC2CCCC=C12)* 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- LXCFILQKKLGQFO-UHFFFAOYSA-N p-hydroxybenzoic acid methyl ester Natural products COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 229950010883 phencyclidine Drugs 0.000 description 1
- 150000002990 phenothiazines Chemical class 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
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
- 229960003415 propylparaben Drugs 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000003196 psychodysleptic agent Substances 0.000 description 1
- 230000000506 psychotropic effect Effects 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000001422 pyrrolinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229940125723 sedative agent Drugs 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 1
- 229910000342 sodium bisulfate Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 description 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- UEUXEKPTXMALOB-UHFFFAOYSA-J tetrasodium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O UEUXEKPTXMALOB-UHFFFAOYSA-J 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 238000011287 therapeutic dose Methods 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 150000005075 thioxanthenes Chemical class 0.000 description 1
- 239000003204 tranquilizing agent Substances 0.000 description 1
- 230000002936 tranquilizing effect Effects 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 210000001364 upper extremity Anatomy 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/12—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 three hetero rings
- C07D471/16—Peri-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious agents
- A61P39/02—Antidotes
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Toxicology (AREA)
- Psychiatry (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 |
|---|---|---|---|
| US07/921,051 US5321023A (en) | 1992-07-29 | 1992-07-29 | Pyridoindolobenzodiazepines and derivatives as antipsychotics |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP931082A2 true HRP931082A2 (en) | 1997-06-30 |
Family
ID=25444846
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR07/921,051A HRP931082A2 (en) | 1992-07-29 | 1993-07-27 | Pyridoindolobenzodiazepines and derivatives as antipsychotics |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US5321023A (fi) |
| EP (1) | EP0652878A1 (fi) |
| JP (1) | JPH08500579A (fi) |
| KR (1) | KR950702562A (fi) |
| CN (1) | CN1100424A (fi) |
| AU (1) | AU4685393A (fi) |
| BR (1) | BR9306896A (fi) |
| CA (1) | CA2141332A1 (fi) |
| CZ (1) | CZ19895A3 (fi) |
| FI (1) | FI950303A (fi) |
| HR (1) | HRP931082A2 (fi) |
| HU (1) | HUT69393A (fi) |
| IL (1) | IL106352A0 (fi) |
| MX (1) | MX9304552A (fi) |
| NO (1) | NO950327L (fi) |
| NZ (1) | NZ254650A (fi) |
| PL (1) | PL307231A1 (fi) |
| RU (1) | RU95107706A (fi) |
| SK (1) | SK40395A3 (fi) |
| TW (1) | TW260670B (fi) |
| WO (1) | WO1994003455A1 (fi) |
| ZA (1) | ZA935486B (fi) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19546297C2 (de) | 1995-12-12 | 2003-12-04 | Temic Bayern Chem Airbag Gmbh | Airbagsystem mit variablem Auslösezeitpunkt |
| US8367655B2 (en) * | 2009-07-03 | 2013-02-05 | Daya Drug Discoveries, Inc. | Pyridoindolobenzox—and thiazepine derivatives and uses thereof |
| EP2964331B1 (en) * | 2013-03-04 | 2019-08-28 | Daya CNS LLC | Pentacyclic pyridoindolo[b,e]azepine derivatives and uses thereof |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3373168A (en) * | 1964-06-02 | 1968-03-12 | Hoffmann La Roche | Certain benzazepinoxyridoindole compounds and their preparation |
| US3457271A (en) * | 1964-06-02 | 1969-07-22 | Hoffmann La Roche | 11-lower alkyl-hexahydro-1-benzazepino (3,2,1-h,i)pyrido(4,3-b)indole |
| US3764684A (en) * | 1971-08-11 | 1973-10-09 | M Finizio | Novel indolobenzazepine derivatives, useful as tranquilizers |
| US3790675A (en) * | 1972-04-19 | 1974-02-05 | Endo Lab | Certain indolobenzazepine derivatives as analgesics |
| US3932650A (en) * | 1973-01-22 | 1976-01-13 | E. I. Du Pont De Nemours & Company | Trans-octahydropyridoindolobenzazepines as central nervous system depressants |
| US3890327A (en) * | 1973-05-11 | 1975-06-17 | Du Pont | Trans-1,2,3,4,4a,8,9,14a-octahydropyrido(r',3':2,3)indolo(1,7-ab)+8 1)benzazepine |
| US3983123A (en) * | 1973-01-22 | 1976-09-28 | Endo Laboratories, Inc. | Trans-octahydropyridoindolobenzazepines |
| CA1026331A (en) * | 1973-12-06 | 1978-02-14 | Joel G. Berger | Substituted indolobenzazepines |
| US4438120A (en) * | 1982-11-12 | 1984-03-20 | E. I. Du Pont De Nemours & Company | Pyridoindolobenzodiazepine tranquilizers |
-
1992
- 1992-07-29 US US07/921,051 patent/US5321023A/en not_active Expired - Lifetime
-
1993
- 1993-07-15 IL IL106352A patent/IL106352A0/xx unknown
- 1993-07-23 KR KR1019950700217A patent/KR950702562A/ko not_active Application Discontinuation
- 1993-07-23 EP EP93917295A patent/EP0652878A1/en not_active Ceased
- 1993-07-23 JP JP6505349A patent/JPH08500579A/ja active Pending
- 1993-07-23 PL PL93307231A patent/PL307231A1/xx unknown
- 1993-07-23 RU RU95107706/14A patent/RU95107706A/ru unknown
- 1993-07-23 CA CA002141332A patent/CA2141332A1/en not_active Abandoned
- 1993-07-23 WO PCT/US1993/006823 patent/WO1994003455A1/en not_active Application Discontinuation
- 1993-07-23 AU AU46853/93A patent/AU4685393A/en not_active Abandoned
- 1993-07-23 HU HU9500193A patent/HUT69393A/hu unknown
- 1993-07-23 SK SK403-95A patent/SK40395A3/sk unknown
- 1993-07-23 NZ NZ254650A patent/NZ254650A/en unknown
- 1993-07-23 BR BR9306896A patent/BR9306896A/pt not_active Application Discontinuation
- 1993-07-23 CZ CZ95198A patent/CZ19895A3/cs unknown
- 1993-07-27 HR HR07/921,051A patent/HRP931082A2/hr not_active Application Discontinuation
- 1993-07-28 MX MX9304552A patent/MX9304552A/es unknown
- 1993-07-29 TW TW082106067A patent/TW260670B/zh active
- 1993-07-29 ZA ZA935486A patent/ZA935486B/xx unknown
- 1993-07-29 CN CN93109416A patent/CN1100424A/zh active Pending
-
1995
- 1995-01-24 FI FI950303A patent/FI950303A/fi not_active Application Discontinuation
- 1995-01-27 NO NO950327A patent/NO950327L/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FI950303A0 (fi) | 1995-01-24 |
| KR950702562A (ko) | 1995-07-29 |
| CA2141332A1 (en) | 1994-02-17 |
| RU95107706A (ru) | 1997-03-20 |
| EP0652878A1 (en) | 1995-05-17 |
| WO1994003455A1 (en) | 1994-02-17 |
| BR9306896A (pt) | 1998-12-08 |
| IL106352A0 (en) | 1993-11-15 |
| HUT69393A (en) | 1995-09-28 |
| MX9304552A (es) | 1994-05-31 |
| NZ254650A (en) | 1996-03-26 |
| NO950327D0 (no) | 1995-01-27 |
| PL307231A1 (en) | 1995-05-15 |
| SK40395A3 (en) | 1995-12-06 |
| NO950327L (no) | 1995-01-27 |
| JPH08500579A (ja) | 1996-01-23 |
| ZA935486B (en) | 1995-01-30 |
| US5321023A (en) | 1994-06-14 |
| FI950303A (fi) | 1995-01-24 |
| HU9500193D0 (en) | 1995-03-28 |
| CZ19895A3 (en) | 1995-11-15 |
| TW260670B (fi) | 1995-10-21 |
| AU4685393A (en) | 1994-03-03 |
| CN1100424A (zh) | 1995-03-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A1OB | Publication of a patent application | ||
| ODBC | Application rejected |