NO761896L - - Google Patents

Info

Publication number: NO761896L
Authority: NO; Norway
Prior art keywords: methyl; fluoro; dibenzo; dihydro; oxazolidinone
Prior art date: 1975-06-06

Application number

NO761896A

Other languages

English (en)

Norwegian (no)

Inventor

E Kyburz

W Aschwanden

Original Assignee

Hoffmann La Roche

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.)

1975-06-06

Filing date

1976-06-04

Publication date

1976-12-07

1976-06-04 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

1976-12-07 Publication of NO761896L publication Critical patent/NO761896L/no

Links

LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 120
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 72
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 65
150000003839 salts Chemical class 0.000 claims description 49
238000000034 method Methods 0.000 claims description 37
230000000694 effects Effects 0.000 claims description 16
238000010992 reflux Methods 0.000 claims description 16
238000003776 cleavage reaction Methods 0.000 claims description 13
230000007017 scission Effects 0.000 claims description 13
230000003287 optical effect Effects 0.000 claims description 12
238000002425 crystallisation Methods 0.000 claims description 10
230000008025 crystallization Effects 0.000 claims description 10
150000001875 compounds Chemical class 0.000 claims description 9
150000002576 ketones Chemical class 0.000 claims description 8
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims description 7
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
238000002360 preparation method Methods 0.000 claims description 6
238000000926 separation method Methods 0.000 claims description 6
239000007787 solid Substances 0.000 claims description 6
NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 5
239000011975 tartaric acid Substances 0.000 claims description 5
229960001367 tartaric acid Drugs 0.000 claims description 5
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 4
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims description 4
229910000147 aluminium phosphate Inorganic materials 0.000 claims description 4
MIOPJNTWMNEORI-UHFFFAOYSA-N camphorsulfonic acid Chemical compound C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-N 0.000 claims description 4
239000012458 free base Substances 0.000 claims description 4
238000010438 heat treatment Methods 0.000 claims description 3
238000004587 chromatography analysis Methods 0.000 claims description 2
239000007788 liquid Substances 0.000 claims description 2
210000000653 nervous system Anatomy 0.000 claims 2
239000000969 carrier Substances 0.000 claims 1
238000011081 inoculation Methods 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
238000002156 mixing Methods 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
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 69
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 46
235000019441 ethanol Nutrition 0.000 description 38
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 36
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 22
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
239000002585 base Substances 0.000 description 17
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
239000000243 solution Substances 0.000 description 16
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 15
239000002253 acid Substances 0.000 description 14
239000011541 reaction mixture Substances 0.000 description 14
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 13
238000003756 stirring Methods 0.000 description 13
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
-1 alkali metal amide Chemical class 0.000 description 10
QRMZSPFSDQBLIX-UHFFFAOYSA-N homovanillic acid Chemical compound COC1=CC(CC(O)=O)=CC=C1O QRMZSPFSDQBLIX-UHFFFAOYSA-N 0.000 description 10
229940098779 methanesulfonic acid Drugs 0.000 description 10
239000012074 organic phase Substances 0.000 description 10
239000000047 product Substances 0.000 description 10
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
229910052938 sodium sulfate Inorganic materials 0.000 description 9
235000011152 sodium sulphate Nutrition 0.000 description 9
238000000354 decomposition reaction Methods 0.000 description 8
239000000155 melt Substances 0.000 description 8
239000000203 mixture Substances 0.000 description 8
239000000126 substance Substances 0.000 description 8
229920002261 Corn starch Polymers 0.000 description 7
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound 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 7
239000013543 active substance Substances 0.000 description 7
239000008120 corn starch Substances 0.000 description 7
229940099112 cornstarch Drugs 0.000 description 7
239000008187 granular material Substances 0.000 description 7
238000001953 recrystallisation Methods 0.000 description 7
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
241000700159 Rattus Species 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
230000000701 neuroleptic effect Effects 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
239000002244 precipitate Substances 0.000 description 6
235000011121 sodium hydroxide Nutrition 0.000 description 6
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
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 5
230000002903 catalepsic effect Effects 0.000 description 5
230000003197 catalytic effect Effects 0.000 description 5
239000012065 filter cake Substances 0.000 description 5
239000008101 lactose Substances 0.000 description 5
230000008018 melting Effects 0.000 description 5
238000002844 melting Methods 0.000 description 5
239000003921 oil Substances 0.000 description 5
235000019198 oils Nutrition 0.000 description 5
238000000746 purification Methods 0.000 description 5
239000002904 solvent Substances 0.000 description 5
239000003826 tablet Substances 0.000 description 5
GAQWDBUWBUOFLS-UHFFFAOYSA-N (7,7-dimethyl-3-oxo-4-bicyclo[2.2.1]heptanyl)methanesulfonic acid;hydrate Chemical compound O.C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C GAQWDBUWBUOFLS-UHFFFAOYSA-N 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
241001465754 Metazoa Species 0.000 description 4
241000699670 Mus sp. Species 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
239000000284 extract Substances 0.000 description 4
239000003960 organic solvent Substances 0.000 description 4
239000000825 pharmaceutical preparation Substances 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
239000011734 sodium Substances 0.000 description 4
239000007858 starting material Substances 0.000 description 4
RMRKBGLDPSCJLF-QGZVFWFLSA-N 1-[(5r)-3-fluoro-8-methyl-5,6-dihydrobenzo[b][1]benzothiepin-5-yl]piperazine Chemical compound N1([C@H]2C3=CC(F)=CC=C3SC3=CC=C(C=C3C2)C)CCNCC1 RMRKBGLDPSCJLF-QGZVFWFLSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
208000009132 Catalepsy Diseases 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
206010047853 Waxy flexibility Diseases 0.000 description 3
229910052783 alkali metal Inorganic materials 0.000 description 3
239000011260 aqueous acid Substances 0.000 description 3
239000011230 binding agent Substances 0.000 description 3
238000009835 boiling Methods 0.000 description 3
CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 3
239000008116 calcium stearate Substances 0.000 description 3
235000013539 calcium stearate Nutrition 0.000 description 3
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
UZVGSSNIUNSOFA-UHFFFAOYSA-N dibenzofuran-1-carboxylic acid Chemical compound O1C2=CC=CC=C2C2=C1C=CC=C2C(=O)O UZVGSSNIUNSOFA-UHFFFAOYSA-N 0.000 description 3
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 3
239000012299 nitrogen atmosphere Substances 0.000 description 3
150000007524 organic acids Chemical class 0.000 description 3
239000012071 phase Substances 0.000 description 3
229910000027 potassium carbonate Inorganic materials 0.000 description 3
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
230000006340 racemization Effects 0.000 description 3
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
239000000454 talc Substances 0.000 description 3
229910052623 talc Inorganic materials 0.000 description 3
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 2
MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 2
LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 2
IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 description 2
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
WVDDGKGOMKODPV-UHFFFAOYSA-N benzyl alcohol Substances OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 2
229940073608 benzyl chloride Drugs 0.000 description 2
239000003874 central nervous system depressant Substances 0.000 description 2
239000013078 crystal Substances 0.000 description 2
230000000994 depressogenic effect Effects 0.000 description 2
VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 2
LNOQURRKNJKKBU-UHFFFAOYSA-N ethyl piperazine-1-carboxylate Chemical compound CCOC(=O)N1CCNCC1 LNOQURRKNJKKBU-UHFFFAOYSA-N 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
239000007903 gelatin capsule Substances 0.000 description 2
229940093915 gynecological organic acid Drugs 0.000 description 2
229910052742 iron Inorganic materials 0.000 description 2
231100000053 low toxicity Toxicity 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
230000014759 maintenance of location Effects 0.000 description 2
239000011976 maleic acid Substances 0.000 description 2
229940098895 maleic acid Drugs 0.000 description 2
229960002510 mandelic acid Drugs 0.000 description 2
150000007522 mineralic acids Chemical class 0.000 description 2
150000004682 monohydrates Chemical class 0.000 description 2
239000003176 neuroleptic agent Substances 0.000 description 2
230000007935 neutral effect Effects 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
235000005985 organic acids Nutrition 0.000 description 2
229960003424 phenylacetic acid Drugs 0.000 description 2
239000003279 phenylacetic acid Substances 0.000 description 2
238000010298 pulverizing process Methods 0.000 description 2
YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
201000000980 schizophrenia Diseases 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
235000002906 tartaric acid Nutrition 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
231100000419 toxicity Toxicity 0.000 description 2
230000001988 toxicity Effects 0.000 description 2
239000008215 water for injection Substances 0.000 description 2
DXDIHODZARUBLA-DTPOWOMPSA-N (2r,3r)-2,3-dibenzoyloxybutanedioic acid;hydrate Chemical compound O.O([C@@H](C(=O)O)[C@@H](OC(=O)C=1C=CC=CC=1)C(O)=O)C(=O)C1=CC=CC=C1 DXDIHODZARUBLA-DTPOWOMPSA-N 0.000 description 1
QIVUCLWGARAQIO-OLIXTKCUSA-N (3s)-n-[(3s,5s,6r)-6-methyl-2-oxo-1-(2,2,2-trifluoroethyl)-5-(2,3,6-trifluorophenyl)piperidin-3-yl]-2-oxospiro[1h-pyrrolo[2,3-b]pyridine-3,6'-5,7-dihydrocyclopenta[b]pyridine]-3'-carboxamide Chemical compound C1([C@H]2[C@H](N(C(=O)[C@@H](NC(=O)C=3C=C4C[C@]5(CC4=NC=3)C3=CC=CN=C3NC5=O)C2)CC(F)(F)F)C)=C(F)C=CC(F)=C1F QIVUCLWGARAQIO-OLIXTKCUSA-N 0.000 description 1
BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
RMRKBGLDPSCJLF-UHFFFAOYSA-N 1-(3-fluoro-8-methyl-5,6-dihydrobenzo[b][1]benzothiepin-5-yl)piperazine Chemical compound C1C2=CC(C)=CC=C2SC2=CC=C(F)C=C2C1N1CCNCC1 RMRKBGLDPSCJLF-UHFFFAOYSA-N 0.000 description 1
IQXXEPZFOOTTBA-UHFFFAOYSA-N 1-benzylpiperazine Chemical compound C=1C=CC=CC=1CN1CCNCC1 IQXXEPZFOOTTBA-UHFFFAOYSA-N 0.000 description 1
ZDZHCHYQNPQSGG-UHFFFAOYSA-N 1-naphthalen-1-ylnaphthalene Chemical group C1=CC=C2C(C=3C4=CC=CC=C4C=CC=3)=CC=CC2=C1 ZDZHCHYQNPQSGG-UHFFFAOYSA-N 0.000 description 1
YONLFQNRGZXBBF-UHFFFAOYSA-N 2,3-dibenzoyloxybutanedioic acid Chemical compound C=1C=CC=CC=1C(=O)OC(C(O)=O)C(C(=O)O)OC(=O)C1=CC=CC=C1 YONLFQNRGZXBBF-UHFFFAOYSA-N 0.000 description 1
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
CQVKMVQRSNNAGO-UHFFFAOYSA-N 2-[4-formyl-3-methyl-n-(2-methylsulfonyloxyethyl)anilino]ethyl methanesulfonate Chemical compound CC1=CC(N(CCOS(C)(=O)=O)CCOS(C)(=O)=O)=CC=C1C=O CQVKMVQRSNNAGO-UHFFFAOYSA-N 0.000 description 1
INGWGCDYAJKXKP-UHFFFAOYSA-N 2-iodo-5-methylbenzoic acid Chemical compound CC1=CC=C(I)C(C(O)=O)=C1 INGWGCDYAJKXKP-UHFFFAOYSA-N 0.000 description 1
CDYDZTYVCIPLHY-UHFFFAOYSA-N 3-(2-chloroethyl)-1,3-oxazolidin-2-one Chemical compound ClCCN1CCOC1=O CDYDZTYVCIPLHY-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
CWNLUWJWWXDUHH-UHFFFAOYSA-N 3-fluoro-8-methyl-6h-benzo[b][1]benzothiepin-5-one Chemical compound O=C1CC2=CC(C)=CC=C2SC2=CC=C(F)C=C21 CWNLUWJWWXDUHH-UHFFFAOYSA-N 0.000 description 1
OKIHXNKYYGUVTE-UHFFFAOYSA-N 4-Fluorothiophenol Chemical compound FC1=CC=C(S)C=C1 OKIHXNKYYGUVTE-UHFFFAOYSA-N 0.000 description 1
XYULFMGUPUNQTE-UHFFFAOYSA-N 5-chloro-3-fluoro-8-methyl-5,6-dihydrobenzo[b][1]benzothiepine Chemical compound ClC1CC2=CC(C)=CC=C2SC2=CC=C(F)C=C21 XYULFMGUPUNQTE-UHFFFAOYSA-N 0.000 description 1
SJVGFKBLUYAEOK-SFHVURJKSA-N 6-[4-[(3S)-3-(3,5-difluorophenyl)-3,4-dihydropyrazole-2-carbonyl]piperidin-1-yl]pyrimidine-4-carbonitrile Chemical compound FC=1C=C(C=C(C=1)F)[C@@H]1CC=NN1C(=O)C1CCN(CC1)C1=CC(=NC=N1)C#N SJVGFKBLUYAEOK-SFHVURJKSA-N 0.000 description 1
244000215068 Acacia senegal Species 0.000 description 1
241000251468 Actinopterygii Species 0.000 description 1
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Natural products OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
LSPHULWDVZXLIL-UHFFFAOYSA-N Camphoric acid Natural products CC1(C)C(C(O)=O)CCC1(C)C(O)=O LSPHULWDVZXLIL-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
BIESMVFSAHOBKT-UHFFFAOYSA-N ClCCC1NC(OC1)=O Chemical compound ClCCC1NC(OC1)=O BIESMVFSAHOBKT-UHFFFAOYSA-N 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 1
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
239000001856 Ethyl cellulose Substances 0.000 description 1
ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
229920000084 Gum arabic Polymers 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
229910052771 Terbium Inorganic materials 0.000 description 1
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
239000000205 acacia gum Substances 0.000 description 1
235000010489 acacia gum Nutrition 0.000 description 1
238000001720 action spectrum Methods 0.000 description 1
230000001154 acute effect Effects 0.000 description 1
239000003513 alkali Substances 0.000 description 1
229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
150000008041 alkali metal carbonates Chemical class 0.000 description 1
229910000102 alkali metal hydride Inorganic materials 0.000 description 1
150000008046 alkali metal hydrides Chemical class 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
239000003708 ampul Substances 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
239000011668 ascorbic acid Substances 0.000 description 1
229960005070 ascorbic acid Drugs 0.000 description 1
235000010323 ascorbic acid Nutrition 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
210000004227 basal ganglia Anatomy 0.000 description 1
230000033228 biological regulation Effects 0.000 description 1
239000000872 buffer Substances 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000001110 calcium chloride Substances 0.000 description 1
229910001628 calcium chloride Inorganic materials 0.000 description 1
LSPHULWDVZXLIL-QUBYGPBYSA-N camphoric acid Chemical compound CC1(C)[C@H](C(O)=O)CC[C@]1(C)C(O)=O LSPHULWDVZXLIL-QUBYGPBYSA-N 0.000 description 1
239000002775 capsule Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000012876 carrier material Substances 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000003795 chemical substances by application Substances 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
229910017052 cobalt Inorganic materials 0.000 description 1
239000010941 cobalt Substances 0.000 description 1
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
NTBIYBAYFBNTCD-UHFFFAOYSA-N dibenzoyl 2,3-dihydroxybutanedioate Chemical compound C=1C=CC=CC=1C(=O)OC(=O)C(O)C(O)C(=O)OC(=O)C1=CC=CC=C1 NTBIYBAYFBNTCD-UHFFFAOYSA-N 0.000 description 1
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
FWCBATIDXGJRMF-UHFFFAOYSA-N dikegulac Natural products C12OC(C)(C)OCC2OC2(C(O)=O)C1OC(C)(C)O2 FWCBATIDXGJRMF-UHFFFAOYSA-N 0.000 description 1
239000000539 dimer Substances 0.000 description 1
229960003638 dopamine Drugs 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
239000008298 dragée Substances 0.000 description 1
239000003814 drug Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
235000019325 ethyl cellulose Nutrition 0.000 description 1
229920001249 ethyl cellulose Polymers 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 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
239000008103 glucose Substances 0.000 description 1
230000002140 halogenating effect Effects 0.000 description 1
FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
150000003840 hydrochlorides Chemical class 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
230000003301 hydrolyzing effect Effects 0.000 description 1
239000005457 ice water Substances 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
TYQCGQRIZGCHNB-JLAZNSOCSA-N l-ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(O)=C(O)C1=O TYQCGQRIZGCHNB-JLAZNSOCSA-N 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
150000002688 maleic acid derivatives Chemical class 0.000 description 1
239000001630 malic acid Substances 0.000 description 1
235000011090 malic acid Nutrition 0.000 description 1
229940099690 malic acid Drugs 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-M methanesulfonate group Chemical class CS(=O)(=O)[O-] AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000011707 mineral Substances 0.000 description 1
VOVZXURTCKPRDQ-CQSZACIVSA-N n-[4-[chloro(difluoro)methoxy]phenyl]-6-[(3r)-3-hydroxypyrrolidin-1-yl]-5-(1h-pyrazol-5-yl)pyridine-3-carboxamide Chemical compound C1[C@H](O)CCN1C1=NC=C(C(=O)NC=2C=CC(OC(F)(F)Cl)=CC=2)C=C1C1=CC=NN1 VOVZXURTCKPRDQ-CQSZACIVSA-N 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
229910000510 noble metal Inorganic materials 0.000 description 1
238000010899 nucleation Methods 0.000 description 1
XULSCZPZVQIMFM-IPZQJPLYSA-N odevixibat Chemical compound C12=CC(SC)=C(OCC(=O)N[C@@H](C(=O)N[C@@H](CC)C(O)=O)C=3C=CC(O)=CC=3)C=C2S(=O)(=O)NC(CCCC)(CCCC)CN1C1=CC=CC=C1 XULSCZPZVQIMFM-IPZQJPLYSA-N 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
230000003204 osmotic effect Effects 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
125000004193 piperazinyl group Chemical group 0.000 description 1
239000003495 polar organic solvent Substances 0.000 description 1
229920001515 polyalkylene glycol Polymers 0.000 description 1
229920000137 polyphosphoric acid Polymers 0.000 description 1
NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
229940100486 rice starch Drugs 0.000 description 1
229960004889 salicylic acid Drugs 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
238000003307 slaughter Methods 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
239000012279 sodium borohydride 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
238000006467 substitution reaction Methods 0.000 description 1
239000001384 succinic acid Substances 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
BISQTCXKVNCDDA-UHFFFAOYSA-N thiepine Chemical compound S1C=CC=CC=C1 BISQTCXKVNCDDA-UHFFFAOYSA-N 0.000 description 1
150000003551 thiepines Chemical class 0.000 description 1
230000007306 turnover Effects 0.000 description 1
229940099259 vaseline Drugs 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- 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
- A61K31/38—Heterocyclic compounds having sulfur as a ring hetero atom
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D337/00—Heterocyclic compounds containing rings of more than six members having one sulfur atom as the only ring hetero atom
- C07D337/02—Seven-membered rings
- C07D337/06—Seven-membered rings condensed with carbocyclic rings or ring systems
- C07D337/10—Seven-membered rings condensed with carbocyclic rings or ring systems condensed with two six-membered rings
- C07D337/14—[b,f]-condensed

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

NO761896A 1975-06-06 1976-06-04 NO761896L (hu)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
CH735375A CH611898A5 (hu)	1975-06-06	1975-06-06
CH350676		1976-03-19

Publications (1)

Publication Number	Publication Date
NO761896L true NO761896L (hu)	1976-12-07

Family

ID=25693196

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO761896A NO761896L (hu)	1975-06-06	1976-06-04

Country Status (21)

Country	Link
US (1)	US4089861A (hu)
JP (1)	JPS51146487A (hu)
AR (1)	AR211168A1 (hu)
AT (1)	AT355026B (hu)
AU (1)	AU499937B2 (hu)
BE (1)	BE842593R (hu)
CA (1)	CA1069506A (hu)
CH (2)	CH613205A5 (hu)
DD (1)	DD125779A6 (hu)
DK (1)	DK244876A (hu)
FI (1)	FI761411A (hu)
FR (1)	FR2313062A2 (hu)
GB (1)	GB1546241A (hu)
HU (1)	HU173216B (hu)
IE (1)	IE44228B1 (hu)
LU (1)	LU75091A1 (hu)
MC (1)	MC1105A1 (hu)
NO (1)	NO761896L (hu)
PL (1)	PL103423B1 (hu)
SE (1)	SE7606387L (hu)
SU (1)	SU637085A3 (hu)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPH01149775A (ja) *	1987-12-07	1989-06-12	Kawaken Fine Chem Co Ltd	光学活性２−メチルピペラジンの製造方法
ES2181774T3 (es) *	1994-04-22	2003-03-01	Koei Chemical Co	Procedimiento para producir n-terc-butil-2-piperazinocarboxamida.
AU740064B2 (en) *	1997-06-18	2001-10-25	H. Lundbeck A/S	Heterocyclic substituted piperidines and uses thereof
US6159990A (en)	1997-06-18	2000-12-12	Synaptic Pharmaceutical Corporation	Oxazolidinones as α1A receptor antagonists
US6228870B1 (en)	1998-11-10	2001-05-08	Merck & Co., Inc.	Oxazolidinones useful as alpha 1a adrenoceptor antagonists
US6319932B1 (en)	1998-11-10	2001-11-20	Merck & Co., Inc.	Oxazolidinones useful as alpha 1A adrenoceptor antagonists

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2412520C2 (de) *	1973-03-30	1982-09-16	F. Hoffmann-La Roche & Co. AG, 4002 Basel	Tricyclische Verbindungen, Verfahren zu deren Herstellung und diese enthaltende Präparate
US3954769A (en) *	1973-03-30	1976-05-04	Hoffman-La Roche Inc.	Dibenzo[b,f]thiepins
US3954764A (en) *	1973-03-30	1976-05-04	Hoffmann-La Roche Inc.	Dibenzo [b,f]thiepins bearing piperazinyl substitution
DD113545A5 (hu) *	1973-03-30	1975-06-12

1975
- 1975-06-06 CH CH44079A patent/CH613205A5/xx not_active IP Right Cessation
- 1975-06-06 CH CH735375A patent/CH611898A5/xx not_active IP Right Cessation
1976
- 1976-04-28 AU AU13423/76A patent/AU499937B2/en not_active Expired
- 1976-05-19 FI FI761411A patent/FI761411A/fi not_active Application Discontinuation
- 1976-05-20 HU HU76HO1906A patent/HU173216B/hu unknown
- 1976-05-26 US US05/690,325 patent/US4089861A/en not_active Expired - Lifetime
- 1976-05-31 MC MC761198A patent/MC1105A1/xx unknown
- 1976-05-31 IE IE1155/76A patent/IE44228B1/en unknown
- 1976-06-03 DK DK244876A patent/DK244876A/da unknown
- 1976-06-03 JP JP51064173A patent/JPS51146487A/ja active Pending
- 1976-06-03 AT AT409376A patent/AT355026B/de not_active IP Right Cessation
- 1976-06-04 BE BE167620A patent/BE842593R/xx active
- 1976-06-04 CA CA254,151A patent/CA1069506A/en not_active Expired
- 1976-06-04 DD DD193199A patent/DD125779A6/xx unknown
- 1976-06-04 SE SE7606387A patent/SE7606387L/xx not_active Application Discontinuation
- 1976-06-04 LU LU75091A patent/LU75091A1/xx unknown
- 1976-06-04 FR FR7617013A patent/FR2313062A2/fr active Granted
- 1976-06-04 SU SU762365997A patent/SU637085A3/ru active
- 1976-06-04 PL PL1976190139A patent/PL103423B1/pl unknown
- 1976-06-04 NO NO761896A patent/NO761896L/no unknown
- 1976-06-04 GB GB23182/76A patent/GB1546241A/en not_active Expired
1977
- 1977-03-09 AR AR266794A patent/AR211168A1/es active

Also Published As

Publication number	Publication date
PL103423B1 (pl)	1979-06-30
CH611898A5 (hu)	1979-06-29
ATA409376A (de)	1979-07-15
JPS51146487A (en)	1976-12-16
LU75091A1 (hu)	1978-01-18
US4089861A (en)	1978-05-16
SU637085A3 (ru)	1978-12-05
HU173216B (hu)	1979-03-28
BE842593R (fr)	1976-12-06
SE7606387L (sv)	1976-12-07
AT355026B (de)	1980-02-11
AU499937B2 (en)	1979-05-03
FI761411A (hu)	1976-12-07
CA1069506A (en)	1980-01-08
MC1105A1 (fr)	1977-02-04
CH613205A5 (hu)	1979-09-14
IE44228L (en)	1976-12-06
DK244876A (da)	1976-12-07
DD125779A6 (hu)	1977-05-18
FR2313062A2 (fr)	1976-12-31
GB1546241A (en)	1979-05-23
AR211168A1 (es)	1977-10-31
IE44228B1 (en)	1981-09-23
FR2313062B2 (hu)	1978-12-15
AU1342376A (en)	1977-11-03

Publication	Publication Date	Title
US4460580A (en)	1984-07-17	N-Alkylated aminoalcohols and their pharmaceutical compositions useful for the treatment of cardiac insufficiency
DK169266B1 (da)	1994-09-26	1,4-disubstituerede piperazinforbindelser, farmaceutiske præparater, der indeholder dem, og fremgangsmåder til deres fremstilling
FR2735127A1 (fr)	1996-12-13	Nouvelles piperazines heteroaromatiques utiles comme medicaments.
RU2116297C1 (ru)	1998-07-27	Производные 1,3-замещенного циклоалкена и циклоалкана в форме смеси изомеров или отдельных изомеров, или их гидраты, или соли
FR2722788A1 (fr)	1996-01-26	Nouvelles piperazides derivees d'aryl piperazine, leurs procedes de preparation, leur utilisation a titre de medicament et les compositions pharmaceutiques les comprenant
JPS6135986B2 (hu)	1986-08-15
WO2010040274A1 (zh)	2010-04-15	新型多巴胺d3受体配体，其制备方法及其医药用途
KR101386387B1 (ko)	2014-04-25	트랜스-1-((1ｒ,3ｓ)-6-클로로-3-페닐인단-1-일)-3,3-디메틸피페라진의 결정성 염기
JPH06340661A (ja)	1994-12-13	オキサゾリジノン化合物
EP0677042A1 (fr)	1995-10-18	Ligands selectifs des recepteurs 5ht 1d?-5ht 1b? derives d'indole-piperazine utiles comme medicaments
EP0269755B1 (en)	1993-11-18	DIBENZ b,e]OXEPIN DERIVATIVE AND PHARMACEUTICAL CONTAINING THE SAME AS ACTIVE INGREDIENT
US4783460A (en)	1988-11-08	Morpholine derivatives, compositions and medicinal uses
NO761896L (hu)	1976-12-07
FR2707639A1 (fr)	1995-01-20	Nouveaux composés indoliques dérivés d'arylamines comme ligands sélectifs des récepteurs 5HT1D et 5HT1B.
NO792113L (no)	1980-01-03	Membranstabiliserende forbindelser som har beta-receptor blokkerende aktivitet, deres fremgangsmaate samt fremgangsmaate for behandling av arrhytmetiske tilstander, og farmasoeytiske preparater som inneholder disse
JPH08283219A (ja)	1996-10-29	アラルキルアミノアルキルアミド誘導体
RU2237668C2 (ru)	2004-10-10	Новые соли морфолинобензамида, способ их получения, фармацевтическая композиция на их основе и способ лечения
US5177077A (en)	1993-01-05	1,4-disubstituted piperazines
US4016280A (en)	1977-04-05	4,4-Diarylpiperidine compositions and use
DE3879402T2 (de)	1993-07-15	Selektive sertonin-aufnahme-inhibitoren.
WO1998042692A1 (fr)	1998-10-01	Piperazines derivees d'amines cycliques, leur preparation et leur application comme medicaments
AU617353B2 (en)	1991-11-28	Pyridylethanolamines
CN111377846B (zh)	2022-05-24	一种哌嗪苯甲酰胺类衍生物及其应用
JPS6130588A (ja)	1986-02-12	ベンゾ〔ｃ〕〔１，８〕ナフチリジン、その製造方法及びその使用、並びにこれらの化合物を含有する調製剤
KR790001871B1 (ko)	1979-12-27	디벤조[b, f] 티에핀 유도체의 제조방법