CH616164A5 - - Google Patents
Download PDFInfo
- Publication number
- CH616164A5 CH616164A5 CH884176A CH884176A CH616164A5 CH 616164 A5 CH616164 A5 CH 616164A5 CH 884176 A CH884176 A CH 884176A CH 884176 A CH884176 A CH 884176A CH 616164 A5 CH616164 A5 CH 616164A5
- Authority
- CH
- Switzerland
- Prior art keywords
- formula
- acids
- thieno
- product
- hydroxy
- Prior art date
Links
- 150000003839 salts Chemical class 0.000 claims description 23
- -1 2-tetrahydropyranyl radical Chemical class 0.000 claims description 19
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 18
- 239000002253 acid Substances 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 16
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 16
- 150000007513 acids Chemical class 0.000 claims description 14
- YVEXKCVGQCMXBV-UHFFFAOYSA-N 10h-thieno[3,2-b][1]benzazepine Chemical compound C1=CC2=CC=CC=C2NC2=C1SC=C2 YVEXKCVGQCMXBV-UHFFFAOYSA-N 0.000 claims description 10
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 9
- 238000010992 reflux Methods 0.000 claims description 9
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical group CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 229910052740 iodine Inorganic materials 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- BBIIPDYZRSNJAM-UHFFFAOYSA-N 5,10-dihydro-4h-thieno[3,2-b][1]benzazepine Chemical compound C1CC2=CC=CC=C2NC2=C1SC=C2 BBIIPDYZRSNJAM-UHFFFAOYSA-N 0.000 claims description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 5
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 5
- 239000008096 xylene Substances 0.000 claims description 5
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 4
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims description 4
- 150000005840 aryl radicals Chemical class 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 239000012312 sodium hydride Substances 0.000 claims description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 3
- 238000005903 acid hydrolysis reaction Methods 0.000 claims description 3
- 229910000102 alkali metal hydride Inorganic materials 0.000 claims description 3
- 150000008046 alkali metal hydrides Chemical class 0.000 claims description 3
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 230000007062 hydrolysis Effects 0.000 claims description 3
- 238000006460 hydrolysis reaction Methods 0.000 claims description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 3
- 239000011707 mineral Substances 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 2
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 claims description 2
- 229940092714 benzenesulfonic acid Drugs 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
- 229940098779 methanesulfonic acid Drugs 0.000 claims description 2
- 150000007522 mineralic acids Chemical class 0.000 claims description 2
- 150000007524 organic acids Chemical class 0.000 claims description 2
- IIVWHGMLFGNMOW-UHFFFAOYSA-N 2-methylpropane Chemical compound C[C](C)C IIVWHGMLFGNMOW-UHFFFAOYSA-N 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 1
- 241001331845 Equus asinus x caballus Species 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- 150000008038 benzoazepines Chemical class 0.000 claims 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 235000015165 citric acid Nutrition 0.000 claims 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid group Chemical class C(CC(O)(C(=O)O)CC(=O)O)(=O)O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 239000000047 product Substances 0.000 description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 5
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
- 235000019341 magnesium sulphate Nutrition 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 239000008194 pharmaceutical composition Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- QFXXARKSLAKVRL-UHFFFAOYSA-N 2-(3-chloropropoxy)oxane Chemical compound ClCCCOC1CCCCO1 QFXXARKSLAKVRL-UHFFFAOYSA-N 0.000 description 3
- ZOITZIOWZUZDCQ-UHFFFAOYSA-N 3-(4,5-dihydrothieno[3,2-b][1]benzazepin-10-yl)propan-1-ol Chemical compound C1CC2=CC=CC=C2N(CCCO)C2=C1SC=C2 ZOITZIOWZUZDCQ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000012047 saturated solution Substances 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 2
- KWDXZIQOFUKRTA-UHFFFAOYSA-N 3-thieno[3,2-b][1]benzazepin-10-ylpropan-1-ol Chemical compound C1=CC2=CC=CC=C2N(CCCO)C2=C1SC=C2 KWDXZIQOFUKRTA-UHFFFAOYSA-N 0.000 description 2
- 208000019901 Anxiety disease Diseases 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000036506 anxiety Effects 0.000 description 2
- RTEXIPZMMDUXMR-UHFFFAOYSA-N benzene;ethyl acetate Chemical compound CCOC(C)=O.C1=CC=CC=C1 RTEXIPZMMDUXMR-UHFFFAOYSA-N 0.000 description 2
- MDHYEMXUFSJLGV-UHFFFAOYSA-N beta-phenethyl acetate Natural products CC(=O)OCCC1=CC=CC=C1 MDHYEMXUFSJLGV-UHFFFAOYSA-N 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000011261 inert gas Substances 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
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 2
- DQFQCHIDRBIESA-UHFFFAOYSA-N 1-benzazepine Chemical compound N1C=CC=CC2=CC=CC=C12 DQFQCHIDRBIESA-UHFFFAOYSA-N 0.000 description 1
- HTGCVLNFLVVCST-UHFFFAOYSA-N 1-piperazin-1-ylethanol Chemical compound CC(O)N1CCNCC1 HTGCVLNFLVVCST-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- WFCSWCVEJLETKA-UHFFFAOYSA-N 2-piperazin-1-ylethanol Chemical compound OCCN1CCNCC1 WFCSWCVEJLETKA-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 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 1
- 206010022998 Irritability Diseases 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 125000000278 alkyl amino alkyl group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 230000001387 anti-histamine Effects 0.000 description 1
- 239000000739 antihistaminic agent Substances 0.000 description 1
- 239000008135 aqueous vehicle Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- ULGGPDHVFPOYQP-UHFFFAOYSA-N chloroform;n,n-diethylethanamine;propan-2-one Chemical compound CC(C)=O.ClC(Cl)Cl.CCN(CC)CC ULGGPDHVFPOYQP-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000001079 digestive effect Effects 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- ZYBWTEQKHIADDQ-UHFFFAOYSA-N ethanol;methanol Chemical compound OC.CCO ZYBWTEQKHIADDQ-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- LHWKGTYIUGLNRX-UHFFFAOYSA-N n-(2,6-diethylphenyl)thiophene-2-carboxamide Chemical compound CCC1=CC=CC(CC)=C1NC(=O)C1=CC=CS1 LHWKGTYIUGLNRX-UHFFFAOYSA-N 0.000 description 1
- 230000003010 neurosedative effect Effects 0.000 description 1
- 239000012053 oil suspension Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 239000004540 pour-on Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-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
- A61P25/20—Hypnotics; Sedatives
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Anesthesiology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7521649A FR2316956A1 (fr) | 1975-07-10 | 1975-07-10 | Nouveaux derives des 4h-thieno-3,2-b-1-benzazepines et leurs sels, procede de preparation et application a titre de medicaments |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH616164A5 true CH616164A5 (en, 2012) | 1980-03-14 |
Family
ID=9157756
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH884176A CH616164A5 (en, 2012) | 1975-07-10 | 1976-07-09 |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US4218375A (en, 2012) |
| JP (1) | JPS5210295A (en, 2012) |
| BE (1) | BE843608A (en, 2012) |
| CA (1) | CA1097632A (en, 2012) |
| CH (1) | CH616164A5 (en, 2012) |
| DE (1) | DE2631077A1 (en, 2012) |
| DK (1) | DK141406B (en, 2012) |
| FR (1) | FR2316956A1 (en, 2012) |
| GB (1) | GB1510929A (en, 2012) |
| IE (1) | IE44349B1 (en, 2012) |
| LU (1) | LU75271A1 (en, 2012) |
| NL (1) | NL7607431A (en, 2012) |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3856910A (en) * | 1950-01-10 | 1974-12-24 | Roussel Uclaf | Novel thienobenzazepines as anti-depressants |
| FR2128030A1 (en) * | 1971-03-01 | 1972-10-20 | Roussel Uclaf | 4-(alkylaminoalkyl) (4h) thieno (3,2-b) (f) benzazepines |
| AR206873A1 (es) * | 1950-01-10 | 1976-08-31 | Roussel Uclaf | Procedimiento para la preparacion de los 4-(alquilamino alquilamino alquilo)9,10-dihidro(4h)tieno(3,2-b)(f)benzazepinas y un compuesto util como intermediario en dicho procedimiento |
| US3267094A (en) * | 1962-09-12 | 1966-08-16 | Colgate Palmolive Co | Morphanthridine derivatives |
| GB1177525A (en) * | 1967-04-13 | 1970-01-14 | Leo Ab | New Heterocyclic Aminoketones of Therapeutic Interest |
-
1975
- 1975-07-10 FR FR7521649A patent/FR2316956A1/fr active Granted
-
1976
- 1976-06-30 BE BE168483A patent/BE843608A/xx unknown
- 1976-06-30 LU LU75271A patent/LU75271A1/xx unknown
- 1976-06-30 US US05/701,152 patent/US4218375A/en not_active Expired - Lifetime
- 1976-07-06 NL NL7607431A patent/NL7607431A/xx not_active Application Discontinuation
- 1976-07-06 JP JP51079547A patent/JPS5210295A/ja active Pending
- 1976-07-08 CA CA256,557A patent/CA1097632A/fr not_active Expired
- 1976-07-09 DE DE19762631077 patent/DE2631077A1/de not_active Withdrawn
- 1976-07-09 CH CH884176A patent/CH616164A5/fr not_active IP Right Cessation
- 1976-07-09 DK DK310176AA patent/DK141406B/da unknown
- 1976-07-12 GB GB28836/76A patent/GB1510929A/en not_active Expired
- 1976-07-12 IE IE1538/76A patent/IE44349B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5210295A (en) | 1977-01-26 |
| DK310176A (en, 2012) | 1977-01-11 |
| FR2316956A1 (fr) | 1977-02-04 |
| IE44349L (en) | 1977-01-10 |
| FR2316956B1 (en, 2012) | 1978-10-06 |
| LU75271A1 (en, 2012) | 1977-03-18 |
| IE44349B1 (en) | 1981-11-04 |
| DK141406B (da) | 1980-03-10 |
| BE843608A (fr) | 1976-12-30 |
| GB1510929A (en) | 1978-05-17 |
| CA1097632A (fr) | 1981-03-17 |
| DK141406C (en, 2012) | 1980-09-08 |
| NL7607431A (nl) | 1977-01-12 |
| DE2631077A1 (de) | 1977-02-03 |
| US4218375A (en) | 1980-08-19 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH628344A5 (fr) | Procede de preparation de nouveaux derives du piperidyl-indole et de leurs sels. | |
| EP0227539A1 (fr) | Nouvelles 4H-triazolo /4,3-a/ /1,4/ benzodiazépines, leur procédé de préparation leur application comme médicaments et les compositions les renfermant | |
| EP0040573B1 (fr) | Dérivés de l'acide 4-hydroxy 3-quinoléine carboxylique substitués en 2, leur préparation, leur application comme médicament, les compositions les renfermant et les intermédiaires nouveaux obtenus | |
| EP0049555A1 (fr) | Nouveaux dérivés de l'acide 2-trifluorométhyl-4-hydroxy-3-quinoline carboxylique et leur procédé de préparation | |
| CA1097647A (fr) | Procede de preparation de nouvelles imidazoquinoleines et de leurs sels | |
| EP0071521B1 (fr) | Nouveaux dérivés du 2-oxo-pyrid-3-yl ou pipéridin-3-yl indole, leurs sels, procédé de préparation, application à titre de médicaments et compositions les renfermant | |
| EP0239436B1 (fr) | Nouveau dérivé tricyclique dénommé acide (chloro-3 méthyl-6 dioxo-5,5 dihydro-6, 11 dibenzo (c,f) thiazépine (1,2) yl-11 amino) -5 pentanoique, son procédé de préparation et les compositions pharmaceutiques qui le contiennent | |
| EP0004494B1 (fr) | Nouveaux dérivés de 1,3-dihydro 3-(1-(2-(2,3-dihydro 1,4-benzo-dioxin-2-yl)2-hydroxy éthyl)pipéridin-4-yl)2H-indol 2-one, leur procédé de préparation, leur application comme médicaments et les compositions pharmaceutiques les renfermant | |
| EP0021924B1 (fr) | Dérivés de l'indole, procédé pour leur préparation, leur application comme médicaments et compositions pharmaceutiques les contenant | |
| CH619935A5 (en, 2012) | ||
| EP0573318A1 (fr) | Nouveaux dérivés de phényle carboxamide isoxazoles et leurs sels, leur procédé de préparation et les nouveaux intermédiaires de ce procédé, leur application comme médicaments et les compositions pharmaceutiques les renfermant | |
| CH616647A5 (en, 2012) | ||
| EP0153230B1 (fr) | Nouveaux dérivés du pyrimido /2,1-b/ benzothiazole et leurs sels, procédé et intermédiaires de préparation, application à titre de médicaments et compositions les renfermant | |
| EP0062580B1 (fr) | Dérivés de l'imidazo(1,2-a)quinoléines | |
| EP0196943B1 (fr) | Nouveaux dérivés 8-thiotétrahydroquinoléines et leurs sels | |
| EP0533573B1 (fr) | Nouveaux dérivés du 3-cyclo alkyl-propen-2-amide, leurs formes tautomères et leurs sels, procédé de préparation, application à titre de médicaments et compositions les renfermant | |
| EP0305298B1 (fr) | Nouvelles imidazo benzodiazépines et leurs sels d'addition avec les acides, leur procédé et les intermédiaires de préparation, leur application comme médicaments et les compositions les renfermant | |
| EP0214004B1 (fr) | Dérivés de l'acide 4-OH quinoléine carboxylique substitué en 2 par un groupement dihydroxylé éventuellement éthérifié ou estérifié, procédé et inter-médiaires de préparation, leur application comme médicaments et les compositions les renfermant | |
| EP0002635B1 (fr) | Procédé de préparation de dérivés de thiéno (2,3-c) et (3,2-c) pyridines, nouveaux dérivés de la thiéno (2,3-c) pyridine obtenus et leur application thérapeutique | |
| FR2641534A1 (fr) | Nouveaux derives de glycine utiles comme medicaments antagonistes du thromboxane a2 et procede pour leur preparation | |
| CH616164A5 (en, 2012) | ||
| EP0210909B1 (fr) | Nouveaux alcoylamino amides et leurs sels, leur préparation, leur application comme médicaments et les compositions les renfermant | |
| FR2619817A1 (fr) | Nouvelles beta carbolines 3-substituees, procede et intermediaires de preparation, application a titre de medicaments et compositions pharmaceutiques les renfermant | |
| EP0061379B1 (fr) | Dérivés de pyridine, leur préparation et leur application en thérapeutique | |
| CA1099290A (fr) | Procede de preparation du 7-amino 6,7 dihydro (5h) benzocycloheptene |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |