NO311085B1 - Nye benzopyranforbindelser, deres fremstilling og farmasöytiske sammensetninger inneholdene dem - Google Patents

Nye benzopyranforbindelser, deres fremstilling og farmasöytiske sammensetninger inneholdene dem Download PDF

Info

Publication number: NO311085B1
Authority: NO; Norway
Prior art keywords: formula; compound; group; compounds; benzyl
Prior art date: 1994-07-06

Application number

NO19952660A

Other languages

English (en)

Norwegian (no)

Other versions

NO952660D0 (no

NO952660L (no

Inventor

Gilbert Lavielle

Thierry Dubuffet

Mark Millan

Adrian Newman-Tancredi

Original Assignee

Adir

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.)

1994-07-06

Filing date

1995-07-05

Publication date

2001-10-08

1995-07-05 Application filed by Adir filed Critical Adir

1995-07-05 Publication of NO952660D0 publication Critical patent/NO952660D0/no

1996-01-08 Publication of NO952660L publication Critical patent/NO952660L/no

2001-10-08 Publication of NO311085B1 publication Critical patent/NO311085B1/no

Links

238000002360 preparation method Methods 0.000 title claims description 51
239000008194 pharmaceutical composition Substances 0.000 title claims description 7
150000001562 benzopyrans Chemical class 0.000 title description 2
-1 pyridinecarbonyl Chemical group 0.000 claims abstract description 25
150000003839 salts Chemical class 0.000 claims abstract description 18
125000000217 alkyl group Chemical group 0.000 claims abstract description 13
239000002253 acid Substances 0.000 claims abstract description 11
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims abstract description 9
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 8
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 6
125000003545 alkoxy group Chemical group 0.000 claims abstract description 5
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 5
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims abstract description 4
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims abstract description 3
125000002252 acyl group Chemical group 0.000 claims abstract description 3
125000000168 pyrrolyl group Chemical group 0.000 claims abstract description 3
150000001875 compounds Chemical class 0.000 claims description 145
238000000034 method Methods 0.000 claims description 56
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 34
239000007858 starting material Substances 0.000 claims description 26
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 19
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 16
125000005843 halogen group Chemical group 0.000 claims description 16
238000000746 purification Methods 0.000 claims description 13
ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 claims description 10
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
102000006902 5-HT2C Serotonin Receptor Human genes 0.000 claims description 8
101150013372 Htr2c gene Proteins 0.000 claims description 8
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 8
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 8
239000012280 lithium aluminium hydride Substances 0.000 claims description 7
125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 6
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 6
125000004093 cyano group Chemical group *C#N 0.000 claims description 6
230000015572 biosynthetic process Effects 0.000 claims description 5
208000035475 disorder Diseases 0.000 claims description 5
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 5
229910000041 hydrogen chloride Inorganic materials 0.000 claims description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
201000000980 schizophrenia Diseases 0.000 claims description 5
238000003786 synthesis reaction Methods 0.000 claims description 5
125000003277 amino group Chemical group 0.000 claims description 4
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 claims description 4
238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 4
229910052736 halogen Inorganic materials 0.000 claims description 4
150000002367 halogens Chemical class 0.000 claims description 4
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239000001257 hydrogen Substances 0.000 claims description 4
238000000926 separation method Methods 0.000 claims description 4
238000010561 standard procedure Methods 0.000 claims description 4
125000001424 substituent group Chemical group 0.000 claims description 4
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 4
208000019901 Anxiety disease Diseases 0.000 claims description 3
230000036506 anxiety Effects 0.000 claims description 3
125000004966 cyanoalkyl group Chemical group 0.000 claims description 3
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238000004519 manufacturing process Methods 0.000 claims description 3
230000008569 process Effects 0.000 claims description 3
QJDUDPQVDAASMV-UHFFFAOYSA-M sodium;ethanethiolate Chemical compound [Na+].CC[S-] QJDUDPQVDAASMV-UHFFFAOYSA-M 0.000 claims description 3
208000027559 Appetite disease Diseases 0.000 claims description 2
208000024172 Cardiovascular disease Diseases 0.000 claims description 2
208000019454 Feeding and Eating disease Diseases 0.000 claims description 2
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208000019695 Migraine disease Diseases 0.000 claims description 2
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150000001412 amines Chemical group 0.000 claims description 2
238000006243 chemical reaction Methods 0.000 claims description 2
238000004140 cleaning Methods 0.000 claims description 2
239000012442 inert solvent Substances 0.000 claims description 2
NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 claims description 2
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
231100000252 nontoxic Toxicity 0.000 claims description 2
230000003000 nontoxic effect Effects 0.000 claims description 2
231100000872 sexual dysfunction Toxicity 0.000 claims description 2
208000019116 sleep disease Diseases 0.000 claims description 2
208000011117 substance-related disease Diseases 0.000 claims description 2
206010008120 Cerebral ischaemia Diseases 0.000 claims 1
239000004480 active ingredient Substances 0.000 claims 1
206010013663 drug dependence Diseases 0.000 claims 1
239000003446 ligand Substances 0.000 claims 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract description 10
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract description 2
125000001475 halogen functional group Chemical group 0.000 abstract 3
125000004442 acylamino group Chemical group 0.000 abstract 2
125000004356 hydroxy functional group Chemical group O* 0.000 abstract 2
125000004953 trihalomethyl group Chemical group 0.000 abstract 2
KYNSBQPICQTCGU-UHFFFAOYSA-N Benzopyrane Chemical compound C1=CC=C2C=CCOC2=C1 KYNSBQPICQTCGU-UHFFFAOYSA-N 0.000 abstract 1
125000004448 alkyl carbonyl group Chemical group 0.000 abstract 1
125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 abstract 1
125000006254 cycloalkyl carbonyl group Chemical group 0.000 abstract 1
125000002541 furyl group Chemical group 0.000 abstract 1
125000005185 naphthylcarbonyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 abstract 1
125000005544 phthalimido group Chemical group 0.000 abstract 1
125000004076 pyridyl group Chemical group 0.000 abstract 1
125000001544 thienyl group Chemical group 0.000 abstract 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 77
239000000047 product Substances 0.000 description 75
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
238000004452 microanalysis Methods 0.000 description 32
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 31
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
239000000243 solution Substances 0.000 description 20
239000000203 mixture Substances 0.000 description 19
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
239000012429 reaction media Substances 0.000 description 17
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
239000003480 eluent Substances 0.000 description 15
238000001704 evaporation Methods 0.000 description 15
230000008020 evaporation Effects 0.000 description 15
239000000377 silicon dioxide Substances 0.000 description 15
238000004440 column chromatography Methods 0.000 description 14
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 12
YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 12
238000000605 extraction Methods 0.000 description 11
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 11
239000002904 solvent Substances 0.000 description 11
238000003756 stirring Methods 0.000 description 11
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
239000012074 organic phase Substances 0.000 description 9
238000010992 reflux Methods 0.000 description 9
WBYWAXJHAXSJNI-VOTSOKGWSA-M trans-cinnamate Chemical compound [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 9
102000049773 5-HT2A Serotonin Receptor Human genes 0.000 description 8
101150104779 HTR2A gene Proteins 0.000 description 8
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 8
229940114081 cinnamate Drugs 0.000 description 8
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
108020003175 receptors Proteins 0.000 description 8
102000005962 receptors Human genes 0.000 description 8
238000001816 cooling Methods 0.000 description 7
238000001914 filtration Methods 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
238000001035 drying Methods 0.000 description 6
235000019441 ethanol Nutrition 0.000 description 6
238000002844 melting Methods 0.000 description 6
230000008018 melting Effects 0.000 description 6
102100036321 5-hydroxytryptamine receptor 2A Human genes 0.000 description 5
101710138091 5-hydroxytryptamine receptor 2A Proteins 0.000 description 5
230000007062 hydrolysis Effects 0.000 description 5
238000006460 hydrolysis reaction Methods 0.000 description 5
102100024959 5-hydroxytryptamine receptor 2C Human genes 0.000 description 4
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VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 4
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
235000011114 ammonium hydroxide Nutrition 0.000 description 4
239000003054 catalyst Substances 0.000 description 4
ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 4
229940079593 drug Drugs 0.000 description 4
239000003814 drug Substances 0.000 description 4
229910000027 potassium carbonate Inorganic materials 0.000 description 4
QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
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FCLZCOCSZQNREK-UHFFFAOYSA-N Pyrrolidine, hydrochloride Chemical compound Cl.C1CCNC1 FCLZCOCSZQNREK-UHFFFAOYSA-N 0.000 description 3
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150000007942 carboxylates Chemical class 0.000 description 3
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238000006352 cycloaddition reaction Methods 0.000 description 3
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RPZAAFUKDPKTKP-UHFFFAOYSA-N n-(methoxymethyl)-1-phenyl-n-(trimethylsilylmethyl)methanamine Chemical compound COCN(C[Si](C)(C)C)CC1=CC=CC=C1 RPZAAFUKDPKTKP-UHFFFAOYSA-N 0.000 description 3
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
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XINQFOMFQFGGCQ-UHFFFAOYSA-L (2-dodecoxy-2-oxoethyl)-[6-[(2-dodecoxy-2-oxoethyl)-dimethylazaniumyl]hexyl]-dimethylazanium;dichloride Chemical compound [Cl-].[Cl-].CCCCCCCCCCCCOC(=O)C[N+](C)(C)CCCCCC[N+](C)(C)CC(=O)OCCCCCCCCCCCC XINQFOMFQFGGCQ-UHFFFAOYSA-L 0.000 description 2
HXTGXYRHXAGCFP-OAQYLSRUSA-N (r)-(2,3-dimethoxyphenyl)-[1-[2-(4-fluorophenyl)ethyl]piperidin-4-yl]methanol Chemical compound COC1=CC=CC([C@H](O)C2CCN(CCC=3C=CC(F)=CC=3)CC2)=C1OC HXTGXYRHXAGCFP-OAQYLSRUSA-N 0.000 description 2
125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
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239000005977 Ethylene Substances 0.000 description 2
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CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
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AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
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239000000546 pharmaceutical excipient Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
230000035790 physiological processes and functions Effects 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
208000020016 psychiatric disease Diseases 0.000 description 1
229940107700 pyruvic acid Drugs 0.000 description 1
238000000611 regression analysis Methods 0.000 description 1
229940076279 serotonin Drugs 0.000 description 1
239000002485 serotonin 2C agonist Substances 0.000 description 1
239000002484 serotonin 2C antagonist Substances 0.000 description 1
230000009329 sexual behaviour Effects 0.000 description 1
230000007958 sleep Effects 0.000 description 1
238000012306 spectroscopic technique Methods 0.000 description 1
239000006190 sub-lingual tablet Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
GTLDTDOJJJZVBW-UHFFFAOYSA-N zinc cyanide Chemical compound [Zn+2].N#[C-].N#[C-] GTLDTDOJJJZVBW-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
- 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
- A61P25/06—Antimigraine agents
- 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
- 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
- A61P25/22—Anxiolytics
- 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
- A61P25/24—Antidepressants
- 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
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
- 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
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis

Landscapes

Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Psychiatry (AREA)
Pain & Pain Management (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Urology & Nephrology (AREA)
Vascular Medicine (AREA)
Addiction (AREA)
Anesthesiology (AREA)
Endocrinology (AREA)
Reproductive Health (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

NO19952660A 1994-07-06 1995-07-05 Nye benzopyranforbindelser, deres fremstilling og farmasöytiske sammensetninger inneholdene dem NO311085B1 (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
FR9408328A FR2722194B1 (fr)	1994-07-06	1994-07-06	Nouveaux derives de benzopyrane, leur procede de preparation et les compositions pharmacuetiques qui les contiennent

Publications (3)

Publication Number	Publication Date
NO952660D0 NO952660D0 (no)	1995-07-05
NO952660L NO952660L (no)	1996-01-08
NO311085B1 true NO311085B1 (no)	2001-10-08

Family

ID=9465049

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO19952660A NO311085B1 (no)	1994-07-06	1995-07-05	Nye benzopyranforbindelser, deres fremstilling og farmasöytiske sammensetninger inneholdene dem

Country Status (16)

Country	Link
US (2)	US5663191A (de)
EP (1)	EP0691342B1 (de)
JP (1)	JP2999139B2 (de)
CN (1)	CN1049660C (de)
AT (1)	ATE179421T1 (de)
AU (1)	AU684165B2 (de)
CA (1)	CA2153195C (de)
DE (1)	DE69509308T2 (de)
DK (1)	DK0691342T3 (de)
ES (1)	ES2133686T3 (de)
FI (1)	FI111945B (de)
FR (1)	FR2722194B1 (de)
GR (1)	GR3030168T3 (de)
NO (1)	NO311085B1 (de)
NZ (1)	NZ272501A (de)
ZA (1)	ZA955631B (de)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5891882A (en) *	1996-12-06	1999-04-06	Abbott Laboratories	Benzopyranopyrrole and benzopyranopyridine α-1 adenergic compounds
FR2764890B1 (fr) *	1997-06-24	1999-08-27	Adir	Nouveaux derives chromeniques, leur procede de preparation et les compositions pharmaceutiques qui les contiennent
US5919802A (en) *	1997-12-05	1999-07-06	Princeton University	Methods of preventing and/or treating temporal lobe epilepsy
TWI274750B (en)	1999-01-12	2007-03-01	Abbott Gmbh & Co Kg	Triazole compounds showing high affinity to dopamine D3 receptor and pharmaceutical composition comprising the same
FR2823752B1 (fr) *	2001-04-18	2004-10-22	Servier Lab	Nouveaux derives de pyrimidin-4-ones, leur procede de preparation et les compositions pharmaceutiques qui les contiennent
GB0118892D0 (en) *	2001-08-02	2001-09-26	Vernalis Res Ltd	Method of treatment
US20040053968A1 (en) *	2001-12-28	2004-03-18	Hartman George D.	Methods and compositions for treating peridontal disease
CN101120002A (zh) *	2005-02-17	2008-02-06	惠氏公司	环烷基稠合的吲哚、苯并噻吩、苯并呋喃和茚衍生物
ATE453622T1 (de) *	2006-04-03	2010-01-15	Hoffmann La Roche	Verfahren zur herstellung von enantiomeren angereicherten cyclischen beta-aryl- oder heteroarylcarbonsäuren
TW200924752A (en) *	2007-09-17	2009-06-16	Organon Nv	Tricyclic heterocyclic derivatives
WO2010069793A1 (en) *	2008-12-16	2010-06-24	F. Hoffmann-La Roche Ag	Process for the preparation of pyrollidine-3-carboxylic acids
FR2948372B1 (fr) *	2009-07-21	2011-07-22	Servier Lab	Nouveaux derives chromeniques, leur procede de preparation et les compositions pharmaceutiques qui les contiennent
CN105111220A (zh) *	2015-09-12	2015-12-02	浙江大学	取代1,4-二氢苯并吡喃[2,3-b]吡咯化合物及其制备方法

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3518272A (en) *	1968-02-05	1970-06-30	Warner Lambert Pharmaceutical	Tetrahydro benzopyranoquinolines and process for their production
US3888946A (en) *	1971-03-17	1975-06-10	Little Inc A	Pyrano benzopyrans
AU560459B2 (en) *	1982-06-01	1987-04-09	Abbott Laboratories	Tetrahydro-benzo(e) isoindolines
US4666916A (en) *	1985-11-08	1987-05-19	Ciba-Geigy Corporation	Hexahydro-(1)-benzo-(pyrano and thiopyrano) (4,3-C)pyridines, useful as serotin-2 blocking agents
DE68926673T2 (de) *	1988-12-15	1997-01-16	Abbott Lab	5-ht-selektive mittel
GB8917333D0 (en) *	1989-07-28	1989-09-13	Merck Sharp & Dohme	Therapeutic agents
FR2687146B1 (fr) *	1992-02-12	1994-04-01	Adir Cie	Nouveaux derives de pyrrolidine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent.

1994
- 1994-07-06 FR FR9408328A patent/FR2722194B1/fr not_active Expired - Fee Related
1995
- 1995-07-04 AU AU24826/95A patent/AU684165B2/en not_active Ceased
- 1995-07-04 CA CA002153195A patent/CA2153195C/fr not_active Expired - Fee Related
- 1995-07-05 NZ NZ272501A patent/NZ272501A/en not_active IP Right Cessation
- 1995-07-05 DK DK95401607T patent/DK0691342T3/da active
- 1995-07-05 ES ES95401607T patent/ES2133686T3/es not_active Expired - Lifetime
- 1995-07-05 NO NO19952660A patent/NO311085B1/no not_active IP Right Cessation
- 1995-07-05 FI FI953308A patent/FI111945B/fi not_active IP Right Cessation
- 1995-07-05 CN CN95109942A patent/CN1049660C/zh not_active Expired - Fee Related
- 1995-07-05 EP EP95401607A patent/EP0691342B1/de not_active Expired - Lifetime
- 1995-07-05 AT AT95401607T patent/ATE179421T1/de active
- 1995-07-05 US US08/498,217 patent/US5663191A/en not_active Expired - Lifetime
- 1995-07-05 DE DE69509308T patent/DE69509308T2/de not_active Expired - Lifetime
- 1995-07-06 ZA ZA955631A patent/ZA955631B/xx unknown
- 1995-07-06 JP JP7170635A patent/JP2999139B2/ja not_active Expired - Fee Related
1997
- 1997-01-21 US US08/786,504 patent/US5723484A/en not_active Expired - Lifetime
1999
- 1999-05-07 GR GR990401249T patent/GR3030168T3/el unknown

Also Published As

Publication number	Publication date
GR3030168T3 (en)	1999-08-31
JP2999139B2 (ja)	2000-01-17
FI953308A7 (fi)	1996-01-07
US5723484A (en)	1998-03-03
CN1049660C (zh)	2000-02-23
CA2153195A1 (fr)	1996-01-07
FR2722194B1 (fr)	1996-08-23
DE69509308D1 (de)	1999-06-02
ES2133686T3 (es)	1999-09-16
ATE179421T1 (de)	1999-05-15
DE69509308T2 (de)	1999-11-25
AU684165B2 (en)	1997-12-04
ZA955631B (en)	1996-02-16
FI953308A0 (fi)	1995-07-05
EP0691342A1 (de)	1996-01-10
JPH0841066A (ja)	1996-02-13
CN1119189A (zh)	1996-03-27
US5663191A (en)	1997-09-02
DK0691342T3 (da)	1999-11-08
FI111945B (fi)	2003-10-15
NO952660D0 (no)	1995-07-05
NZ272501A (en)	1996-03-26
NO952660L (no)	1996-01-08
FR2722194A1 (fr)	1996-01-12
EP0691342B1 (de)	1999-04-28
CA2153195C (fr)	2004-06-15
AU2482695A (en)	1996-01-18

Legal Events

Date	Code	Title	Description
2015-02-23	MM1K	Lapsed by not paying the annual fees

Publication	Publication Date	Title
DE60004066T2 (de)	2004-04-15	Benzofurylpiperazine: 5-ht2c serotoninrezeptor agonisten
AU2017269256B2 (en)	2021-02-25	Aminoacylindazole immunomodulators for treatment of autoimmune diseases
AU2003243160B2 (en)	2009-02-05	1,2,3,4,7,8-hexahydro-6H-[1,4]diazepino[6,7,1-ij]quinoline derivatives as antipsychotic and antiobesity agents
CZ283680B6 (cs)	1998-06-17	Nové azaheterocyklylmethyl-chromany
WO1997047601A1 (en)	1997-12-18	Fused heterocyclic compounds and medicinal uses thereof
NO165838B (no)	1991-01-07	Analogifremgangsmaate for fremstilling av terapeutisk aktive substituerte trans-1,2-diamino-cykloheksylamidforbindelser.
LV12630B (en)	2001-08-20	2-aminoindans as selective dopamine d3 ligands
US5723484A (en)	1998-03-03	Benzopyran compounds as 5-HT2C receptor antagonists
KR20070083843A (ko)	2007-08-24	아자인돌 카르복사미드
AU2018375308A1 (en)	2020-06-25	Pyranopyrazole and pyrazolopyridine immunomodulators for treatment of autoimmune diseases
JP7387926B2 (ja)	2023-11-28	選択的エストロゲン受容体分解剤の調製のためのプロセス
SK361292A3 (en)	1997-09-10	Piperidylmethyl-substituted chroman derivatives, process for producing them, their use and pharmaceutical composition containg same
JPH06287190A (ja)	1994-10-11	新規な３−アミノクロマンスピロ化合物、それらの製造法およびそれらを含む薬学組成物
JP2020522504A (ja)	2020-07-30	多環式化合物およびそれらの用途
Marchalín et al.	2007	An expedient synthesis of 7 (S)-ethyl-8 (R or S)-indolizidinols based on a thiophene reductive desulfurization
MXPA05002838A (es)	2005-08-16	Derivados de cicloalquilamina antidepresiva de benzodioxanos fusionados con heterociclos.
JP3541952B2 (ja)	2004-07-14	４−アリールイソインドール鎮痛薬
KR910002564B1 (ko)	1991-04-26	헥사하이드로피롤로[2,1-a]이소퀴놀린 유도체의 제조방법
KR20050042192A (ko)	2005-05-04	헤테로고리-접합된 벤조디옥산의 항울성 피페리딘 유도체
JP4823221B2 (ja)	2011-11-24	新規な不飽和四環式テトラヒドロフラン誘導体
AU781663B2 (en)	2005-06-02	New pyrimidin-4-one compounds, a process for their preparation and pharmaceutical compositions containing them
EP4508028B1 (de)	2026-03-11	Neuartige substituierte 4-amino-4-oxo-but-2-enyl-derivate, verfahren zu ihrer herstellung und therapeutische verwendungen davon
KR100491596B1 (ko)	2005-05-27	피리미딘-4-온 화합물, 이들을 제조하는 방법 및 이들을함유하는 약제학적 조성물
EP2406217A1 (de)	2012-01-18	Tricyclische heterocyclische derivate
CA2576332A1 (en)	2006-07-13	Phenyl diazepane carboxamides and annelated phenyl piperazine carboxamides containing oxygen and used as dopamine d3 antagonists