CH513806A - Verfahren zur Herstellung von tricyclischen Verbindungen - Google Patents
Verfahren zur Herstellung von tricyclischen VerbindungenInfo
- Publication number
- CH513806A CH513806A CH1768070A CH1768070A CH513806A CH 513806 A CH513806 A CH 513806A CH 1768070 A CH1768070 A CH 1768070A CH 1768070 A CH1768070 A CH 1768070A CH 513806 A CH513806 A CH 513806A
- Authority
- CH
- Switzerland
- Prior art keywords
- methyl
- dibenzo
- dihydro
- formula
- cycloheptene
- Prior art date
Links
- 230000001430 anti-depressive effect Effects 0.000 title description 4
- 150000003839 salts Chemical class 0.000 claims abstract description 12
- -1 adrenolytics Substances 0.000 claims abstract description 9
- 239000000203 mixture Substances 0.000 claims abstract description 9
- 150000001875 compounds Chemical class 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 12
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 5
- 230000003287 optical effect Effects 0.000 claims description 4
- 239000007858 starting material Substances 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 2
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract description 5
- 230000001078 anti-cholinergic effect Effects 0.000 abstract description 3
- 230000002908 adrenolytic effect Effects 0.000 abstract description 2
- QPJORFLSOJAUNL-UHFFFAOYSA-N dibenzo[a,d][7]annulene Chemical compound C1=CC2=CC=CC=C2CC2=CC=CC=C21 QPJORFLSOJAUNL-UHFFFAOYSA-N 0.000 abstract description 2
- 231100000053 low toxicity Toxicity 0.000 abstract description 2
- 150000001204 N-oxides Chemical class 0.000 abstract 1
- 239000000935 antidepressant agent Substances 0.000 abstract 1
- 229940005513 antidepressants Drugs 0.000 abstract 1
- 229940125715 antihistaminic agent Drugs 0.000 abstract 1
- 239000000739 antihistaminic agent Substances 0.000 abstract 1
- PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 abstract 1
- 229960005015 local anesthetics Drugs 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 27
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 206010039424 Salivary hypersecretion Diseases 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 239000000155 melt Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 208000026451 salivation Diseases 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- OAGMNEZLAIVVGD-UHFFFAOYSA-N 11-chloro-4-methyl-11h-dibenzo[1,2-a:1',2'-e][7]annulene Chemical compound ClC1C2=CC=CC=C2C=CC2=C1C=CC=C2C OAGMNEZLAIVVGD-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 229960000836 amitriptyline Drugs 0.000 description 3
- KRMDCWKBEZIMAB-UHFFFAOYSA-N amitriptyline Chemical compound C1CC2=CC=CC=C2C(=CCCN(C)C)C2=CC=CC=C21 KRMDCWKBEZIMAB-UHFFFAOYSA-N 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
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- QCHFTSOMWOSFHM-WPRPVWTQSA-N (+)-Pilocarpine Chemical compound C1OC(=O)[C@@H](CC)[C@H]1CC1=CN=CN1C QCHFTSOMWOSFHM-WPRPVWTQSA-N 0.000 description 2
- NYYRRBOMNHUCLB-UHFFFAOYSA-N 3-chloro-n,n-dimethylpropan-1-amine Chemical compound CN(C)CCCCl NYYRRBOMNHUCLB-UHFFFAOYSA-N 0.000 description 2
- LAYUZOBOKPCWSY-UHFFFAOYSA-N 4-methyl-6,11-dihydro-5h-dibenzo[1,2-a:2',1'-d][7]annulen-11-ol Chemical compound OC1C2=CC=CC=C2CCC2=C1C=CC=C2C LAYUZOBOKPCWSY-UHFFFAOYSA-N 0.000 description 2
- XGGKPBPLHQKZAU-UHFFFAOYSA-N 4-methyldibenzo[1,2-a:2',1'-d][7]annulen-11-one Chemical compound C1=CC2=CC=CC=C2C(=O)C2=C1C(C)=CC=C2 XGGKPBPLHQKZAU-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
- 206010015995 Eyelid ptosis Diseases 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- QCHFTSOMWOSFHM-UHFFFAOYSA-N SJ000285536 Natural products C1OC(=O)C(CC)C1CC1=CN=CN1C QCHFTSOMWOSFHM-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
- 230000007059 acute toxicity Effects 0.000 description 2
- 231100000403 acute toxicity Toxicity 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- XHRNQDMNINGCES-UHFFFAOYSA-N cyclohept-4-en-1-one Chemical compound O=C1CCC=CCC1 XHRNQDMNINGCES-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 230000026030 halogenation Effects 0.000 description 2
- 238000005658 halogenation reaction Methods 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 230000004899 motility Effects 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- 229960001416 pilocarpine Drugs 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 201000003004 ptosis Diseases 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 description 2
- 239000012279 sodium borohydride Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 2
- 239000011975 tartaric acid Substances 0.000 description 2
- 235000002906 tartaric acid Nutrition 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-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 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- AGQMLYXXEXJKGK-UHFFFAOYSA-N 11-chloro-4-methyl-6,11-dihydro-5h-dibenzo[2,1-b:2',1'-f][7]annulene Chemical compound ClC1C2=CC=CC=C2CCC2=C1C=CC=C2C AGQMLYXXEXJKGK-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
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- XBEZGXHZOGGCAH-UHFFFAOYSA-N 4-methyl-11h-dibenzo[1,2-a:1',2'-e][7]annulen-11-ol Chemical compound OC1C2=CC=CC=C2C=CC2=C1C=CC=C2C XBEZGXHZOGGCAH-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- 206010002091 Anaesthesia Diseases 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 229940123445 Tricyclic antidepressant Drugs 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 230000009194 climbing Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- ZXIJMRYMVAMXQP-UHFFFAOYSA-N cycloheptene Chemical compound C1CCC=CCC1 ZXIJMRYMVAMXQP-UHFFFAOYSA-N 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- NGPAITITALWALP-UHFFFAOYSA-M magnesium;n,n-dimethylpropan-1-amine;chloride Chemical compound [Mg+2].[Cl-].CN(C)CC[CH2-] NGPAITITALWALP-UHFFFAOYSA-M 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- ZFGYZAXGWJAKOI-UHFFFAOYSA-N n,n-dimethyl-3-(4-methyl-11h-dibenzo[1,2-a:1',2'-e][7]annulen-11-yl)propan-1-amine Chemical compound C1=CC2=C(C)C=CC=C2C(CCCN(C)C)C2=CC=CC=C21 ZFGYZAXGWJAKOI-UHFFFAOYSA-N 0.000 description 1
- 210000000653 nervous system Anatomy 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 229940001470 psychoactive drug Drugs 0.000 description 1
- 239000004089 psychotropic agent Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 210000003296 saliva Anatomy 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 239000003029 tricyclic antidepressant agent Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/32—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing keto groups
- C07C65/38—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing keto groups having unsaturation outside the aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
- C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
- C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
- C07C13/54—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings
- C07C13/547—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings at least one ring not being six-membered, the other rings being at the most six-membered
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C63/00—Compounds having carboxyl groups bound to a carbon atoms of six-membered aromatic rings
- C07C63/33—Polycyclic acids
- C07C63/331—Polycyclic acids with all carboxyl groups bound to non-condensed rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/30—Ortho- or ortho- and peri-condensed systems containing three rings containing seven-membered rings
- C07C2603/32—Dibenzocycloheptenes; Hydrogenated dibenzocycloheptenes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1768070A CH513806A (de) | 1968-05-03 | 1968-05-03 | Verfahren zur Herstellung von tricyclischen Verbindungen |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH661268A CH501581A (de) | 1968-05-03 | 1968-05-03 | Verfahren zur Herstellung von tricyclischen Verbindungen |
| CH1768070A CH513806A (de) | 1968-05-03 | 1968-05-03 | Verfahren zur Herstellung von tricyclischen Verbindungen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH513806A true CH513806A (de) | 1971-10-15 |
Family
ID=4312293
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1768070A CH513806A (de) | 1968-05-03 | 1968-05-03 | Verfahren zur Herstellung von tricyclischen Verbindungen |
| CH1768270A CH513807A (de) | 1968-05-03 | 1968-05-03 | Verfahren zur Herstellung von tricyclischen Verbindungen |
| CH661268A CH501581A (de) | 1968-05-03 | 1968-05-03 | Verfahren zur Herstellung von tricyclischen Verbindungen |
| CH1768570A CH513808A (de) | 1968-05-03 | 1968-05-03 | Verfahren zur Herstellung von tricyclischen Verbindungen |
Family Applications After (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1768270A CH513807A (de) | 1968-05-03 | 1968-05-03 | Verfahren zur Herstellung von tricyclischen Verbindungen |
| CH661268A CH501581A (de) | 1968-05-03 | 1968-05-03 | Verfahren zur Herstellung von tricyclischen Verbindungen |
| CH1768570A CH513808A (de) | 1968-05-03 | 1968-05-03 | Verfahren zur Herstellung von tricyclischen Verbindungen |
Country Status (16)
| Country | Link |
|---|---|
| JP (1) | JPS4939675B1 (en:Method) |
| AT (9) | AT296956B (en:Method) |
| BE (1) | BE732328A (en:Method) |
| BR (1) | BR6908384D0 (en:Method) |
| CA (1) | CA972752A (en:Method) |
| CH (4) | CH513806A (en:Method) |
| DE (1) | DE1922280C3 (en:Method) |
| ES (1) | ES366688A1 (en:Method) |
| FR (1) | FR2007772A1 (en:Method) |
| GB (2) | GB1274261A (en:Method) |
| IE (1) | IE33452B1 (en:Method) |
| IL (1) | IL32058A (en:Method) |
| MY (1) | MY7300181A (en:Method) |
| NL (1) | NL161439C (en:Method) |
| NO (1) | NO125628B (en:Method) |
| SE (1) | SE365790B (en:Method) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5321654A (en) * | 1976-08-11 | 1978-02-28 | Matsushita Electric Works Ltd | Motor driven tooth brush |
| JPS5321655A (en) * | 1976-08-11 | 1978-02-28 | Matsushita Electric Works Ltd | Motor driven tooth brush |
| CA1160219A (en) * | 1981-01-16 | 1984-01-10 | Werner Aschwanden | Cycloheptene derivatives |
| CA3069699A1 (en) * | 2017-07-13 | 2019-01-17 | Tonix Pharmaceuticals Holding Corp. | Analogs of cyclobenzaprine and amitryptilene |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE630063A (en:Method) * | 1962-03-23 |
-
1968
- 1968-05-03 CH CH1768070A patent/CH513806A/de not_active IP Right Cessation
- 1968-05-03 CH CH1768270A patent/CH513807A/de not_active IP Right Cessation
- 1968-05-03 CH CH661268A patent/CH501581A/de not_active IP Right Cessation
- 1968-05-03 CH CH1768570A patent/CH513808A/de not_active IP Right Cessation
- 1968-06-28 NO NO2577/68A patent/NO125628B/no unknown
- 1968-06-28 SE SE08965/68A patent/SE365790B/xx unknown
-
1969
- 1969-04-14 NL NL6905705.A patent/NL161439C/xx active
- 1969-04-22 IL IL32058A patent/IL32058A/xx unknown
- 1969-04-28 BR BR208384/69A patent/BR6908384D0/pt unknown
- 1969-04-28 CA CA049,911A patent/CA972752A/en not_active Expired
- 1969-04-30 DE DE1922280A patent/DE1922280C3/de not_active Expired
- 1969-04-30 BE BE732328D patent/BE732328A/xx unknown
- 1969-05-01 GB GB22175/69A patent/GB1274261A/en not_active Expired
- 1969-05-01 GB GB28708/71A patent/GB1274265A/en not_active Expired
- 1969-05-01 IE IE611/69A patent/IE33452B1/xx unknown
- 1969-05-02 AT AT1158370A patent/AT296956B/de not_active IP Right Cessation
- 1969-05-02 AT AT1158870A patent/AT296958B/de not_active IP Right Cessation
- 1969-05-02 AT AT1158770A patent/AT299153B/de not_active IP Right Cessation
- 1969-05-02 AT AT1158970A patent/AT296959B/de not_active IP Right Cessation
- 1969-05-02 AT AT1158470A patent/AT296957B/de not_active IP Right Cessation
- 1969-05-02 AT AT1158570A patent/AT297679B/de active
- 1969-05-02 AT AT1158670A patent/AT294036B/de not_active IP Right Cessation
- 1969-05-02 AT AT425469A patent/AT296954B/de not_active IP Right Cessation
- 1969-05-02 JP JP44034472A patent/JPS4939675B1/ja active Pending
- 1969-05-02 ES ES366688A patent/ES366688A1/es not_active Expired
- 1969-05-02 FR FR6914017A patent/FR2007772A1/fr not_active Withdrawn
- 1969-05-02 AT AT1158270A patent/AT296955B/de not_active IP Right Cessation
-
1973
- 1973-12-30 MY MY181/73A patent/MY7300181A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CH513808A (de) | 1971-10-15 |
| AT296958B (de) | 1972-03-10 |
| CA972752A (en) | 1975-08-12 |
| NL161439B (nl) | 1979-09-17 |
| CH501581A (de) | 1971-01-15 |
| JPS4939675B1 (en:Method) | 1974-10-28 |
| IE33452B1 (en) | 1974-07-10 |
| NO125628B (en:Method) | 1972-10-09 |
| BR6908384D0 (pt) | 1973-01-04 |
| DE1922280B2 (de) | 1979-05-03 |
| ES366688A1 (es) | 1971-04-16 |
| IL32058A0 (en) | 1969-06-25 |
| AT296956B (de) | 1972-03-10 |
| AT294036B (de) | 1971-11-10 |
| NL6905705A (en:Method) | 1969-11-05 |
| CH513807A (de) | 1971-10-15 |
| MY7300181A (en) | 1973-12-31 |
| NL161439C (nl) | 1980-02-15 |
| IE33452L (en) | 1969-11-03 |
| FR2007772A1 (en:Method) | 1970-01-09 |
| AT297679B (de) | 1972-04-10 |
| DE1922280A1 (de) | 1969-11-20 |
| AT296954B (de) | 1972-03-10 |
| DE1922280C3 (de) | 1980-01-17 |
| AT299153B (de) | 1972-06-12 |
| SE365790B (en:Method) | 1974-04-01 |
| AT296959B (de) | 1972-03-10 |
| GB1274265A (en) | 1972-05-17 |
| AT296957B (de) | 1972-03-10 |
| GB1274261A (en) | 1972-05-17 |
| BE732328A (en:Method) | 1969-10-30 |
| IL32058A (en) | 1974-01-14 |
| AT296955B (de) | 1972-03-10 |
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Legal Events
| Date | Code | Title | Description |
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| PL | Patent ceased |