DE2360545A1 - Neue trialkoxyaroyldiamine - Google Patents
Neue trialkoxyaroyldiamineInfo
- Publication number
- DE2360545A1 DE2360545A1 DE19732360545 DE2360545A DE2360545A1 DE 2360545 A1 DE2360545 A1 DE 2360545A1 DE 19732360545 DE19732360545 DE 19732360545 DE 2360545 A DE2360545 A DE 2360545A DE 2360545 A1 DE2360545 A1 DE 2360545A1
- Authority
- DE
- Germany
- Prior art keywords
- groups
- group
- carbon atoms
- radicals
- substituted
- Prior art date
- Legal status (The legal status 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 status listed.)
- Pending
Links
- 150000004985 diamines Chemical class 0.000 title description 2
- -1 benzaniino Chemical group 0.000 claims description 105
- 150000001875 compounds Chemical class 0.000 claims description 53
- 125000004432 carbon atom Chemical group C* 0.000 claims description 47
- 238000000034 method Methods 0.000 claims description 28
- 125000000217 alkyl group Chemical group 0.000 claims description 22
- 239000000126 substance Substances 0.000 claims description 22
- 125000003545 alkoxy group Chemical group 0.000 claims description 18
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 15
- 229920006395 saturated elastomer Polymers 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 12
- 238000002360 preparation method Methods 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 239000003814 drug Substances 0.000 claims description 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 229910052794 bromium Inorganic materials 0.000 claims description 8
- 239000000460 chlorine Substances 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- FQUYSHZXSKYCSY-UHFFFAOYSA-N 1,4-diazepane Chemical group C1CNCCNC1 FQUYSHZXSKYCSY-UHFFFAOYSA-N 0.000 claims description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 125000001041 indolyl group Chemical group 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 5
- 125000003277 amino group Chemical group 0.000 claims description 5
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 5
- 125000000335 thiazolyl group Chemical group 0.000 claims description 5
- 125000001544 thienyl group Chemical group 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 125000002541 furyl group Chemical group 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 125000006239 protecting group Chemical group 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 125000004442 acylamino group Chemical group 0.000 claims description 3
- 125000004423 acyloxy group Chemical group 0.000 claims description 3
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 claims description 3
- 239000000969 carrier Substances 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 229940126601 medicinal product Drugs 0.000 claims description 3
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 3
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 125000004417 unsaturated alkyl group Chemical group 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 5
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims 4
- 125000001624 naphthyl group Chemical group 0.000 claims 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims 2
- 229910052731 fluorine Inorganic materials 0.000 claims 2
- 239000011737 fluorine Substances 0.000 claims 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 2
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 2
- ZEJLTSHKOAEJME-UHFFFAOYSA-N N-acetamido-N-(propanoylamino)butanamide Chemical compound C(C)(=O)NN(C(CCC)=O)NC(CC)=O ZEJLTSHKOAEJME-UHFFFAOYSA-N 0.000 claims 1
- 125000004663 dialkyl amino group Chemical group 0.000 claims 1
- 125000004915 dibutylamino group Chemical group C(CCC)N(CCCC)* 0.000 claims 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
- 125000004914 dipropylamino group Chemical group C(CC)N(CCC)* 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 125000002950 monocyclic group Chemical group 0.000 claims 1
- 239000008024 pharmaceutical diluent Substances 0.000 claims 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 66
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 63
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 56
- 229930040373 Paraformaldehyde Natural products 0.000 description 50
- 229920002866 paraformaldehyde Polymers 0.000 description 50
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 40
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 38
- 239000002904 solvent Substances 0.000 description 32
- 229960004592 isopropanol Drugs 0.000 description 28
- 238000003756 stirring Methods 0.000 description 28
- 238000010992 reflux Methods 0.000 description 27
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 17
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 14
- 150000003254 radicals Chemical class 0.000 description 14
- QYQBLZDLNPLGCY-UHFFFAOYSA-N piperazin-1-yl-(3,4,5-trimethoxyphenyl)methanone Chemical compound COC1=C(OC)C(OC)=CC(C(=O)N2CCNCC2)=C1 QYQBLZDLNPLGCY-UHFFFAOYSA-N 0.000 description 13
- 239000002585 base Substances 0.000 description 10
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
- 239000003513 alkali Substances 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 150000008064 anhydrides Chemical class 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 5
- 239000013543 active substance Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000003826 tablet Substances 0.000 description 5
- WYJOVVXUZNRJQY-UHFFFAOYSA-N 2-Acetylthiophene Chemical compound CC(=O)C1=CC=CS1 WYJOVVXUZNRJQY-UHFFFAOYSA-N 0.000 description 4
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 4
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 4
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- 230000010933 acylation Effects 0.000 description 4
- 238000005917 acylation reaction Methods 0.000 description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 239000001913 cellulose Chemical class 0.000 description 4
- 229920002678 cellulose Chemical class 0.000 description 4
- 239000012442 inert solvent Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 229910052763 palladium Inorganic materials 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 150000003512 tertiary amines Chemical class 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 125000002252 acyl group Chemical group 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
- 238000001816 cooling Methods 0.000 description 3
- 239000002537 cosmetic Substances 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- LNTHITQWFMADLM-UHFFFAOYSA-N gallic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 238000001990 intravenous administration Methods 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 239000008194 pharmaceutical composition Substances 0.000 description 3
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 239000011732 tocopherol Substances 0.000 description 3
- 229930003799 tocopherol Natural products 0.000 description 3
- 235000019149 tocopherols Nutrition 0.000 description 3
- 150000003626 triacylglycerols Chemical class 0.000 description 3
- 229910052720 vanadium Inorganic materials 0.000 description 3
- QUEDXNHFTDJVIY-UHFFFAOYSA-N γ-tocopherol Chemical class OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-UHFFFAOYSA-N 0.000 description 3
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
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- 241001465754 Metazoa Species 0.000 description 2
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- 238000007327 hydrogenolysis reaction Methods 0.000 description 2
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- 238000003786 synthesis reaction Methods 0.000 description 2
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- 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
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- 238000011282 treatment Methods 0.000 description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/192—Radicals derived from carboxylic acids from aromatic carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D307/80—Radicals substituted by oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Furan Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT1044372 | 1972-12-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2360545A1 true DE2360545A1 (de) | 1974-06-12 |
Family
ID=3622380
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19732360545 Pending DE2360545A1 (de) | 1972-12-07 | 1973-12-05 | Neue trialkoxyaroyldiamine |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS4993334A (en, 2012) |
| BE (1) | BE808337A (en, 2012) |
| DD (1) | DD109632A5 (en, 2012) |
| DE (1) | DE2360545A1 (en, 2012) |
| ES (2) | ES421159A1 (en, 2012) |
| FR (1) | FR2209560A1 (en, 2012) |
| NL (1) | NL7316714A (en, 2012) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0219625A1 (en) * | 1985-10-15 | 1987-04-29 | Merrell Dow Pharmaceuticals Inc. | Cardiotonic heterocyclocarbonyl- and acetyl-thiazolones |
| FR2637500A1 (fr) * | 1988-10-11 | 1990-04-13 | Scras | Medicaments a base de nouveaux derives de la carbonyl-2 n, n'-di-(trimethoxybenzoyle) piperazine |
| FR2637499A1 (fr) * | 1988-10-11 | 1990-04-13 | Scras | Medicaments a base de nouveaux derives de la methoxycarbonyl-2 n, n'-di-(trimethoxybenzoyle) piperazine |
| FR2645859A1 (fr) * | 1989-04-15 | 1990-10-19 | Scras | Derives di-substitues des n,n(prime)-ditrimethoxybenzoyle piperazines ainsi que leur procede de preparation |
| EP0168003B1 (en) * | 1984-07-06 | 1991-04-03 | Otsuka Pharmaceutical Co., Ltd. | Oxindol compounds, compositions containing same and processes for preparing same |
| WO1996016052A3 (en) * | 1994-11-17 | 1996-08-01 | Molecular Geriatrics Corp | Certain substituted 1-aryl-3-piperazin-1'-yl propanones |
| US6214994B1 (en) | 1997-04-21 | 2001-04-10 | Molecular Geriatrics Corporation | Certain substituted 1-aryl-3-piperazin-1′-yl propanones |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2474031A1 (fr) * | 1980-01-21 | 1981-07-24 | Delalande Sa | Nouveaux derives de la trimethoxy-3,4,5 cinnamoyle piperazine, leurs sels, leur procede de preparation et leur application en therapeutique |
| FR2497512A2 (fr) * | 1981-01-07 | 1982-07-09 | Delalande Sa | Nouveaux derives de la trimethoxy-3,4,5 cinnamoyl piperazine, leurs sels, leur procede de preparation et leur application en therapeutique |
| WO1982003861A1 (en) * | 1981-05-08 | 1982-11-11 | Tominaga Michiaki | Aniline derivatives,process for their preparation,and cardiotonics |
| JP2573195B2 (ja) * | 1986-09-30 | 1997-01-22 | エーザイ株式会社 | 環状アミン誘導体 |
| GB8823041D0 (en) * | 1988-09-30 | 1988-11-09 | Lilly Sa | Organic compounds & their use as pharmaceuticals |
| CA2015678A1 (en) * | 1989-04-28 | 1990-10-28 | Norio Nakamura | N-acryloylpiperazine derivatives, their preparation and their use as paf antagonists |
-
1973
- 1973-11-29 FR FR7342546A patent/FR2209560A1/fr not_active Withdrawn
- 1973-12-05 DD DD17511573A patent/DD109632A5/xx unknown
- 1973-12-05 ES ES421159A patent/ES421159A1/es not_active Expired
- 1973-12-05 DE DE19732360545 patent/DE2360545A1/de active Pending
- 1973-12-05 ES ES421160A patent/ES421160A1/es not_active Expired
- 1973-12-06 BE BE6044387A patent/BE808337A/xx unknown
- 1973-12-06 NL NL7316714A patent/NL7316714A/xx unknown
- 1973-12-07 JP JP48137255A patent/JPS4993334A/ja active Pending
Cited By (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0168003B1 (en) * | 1984-07-06 | 1991-04-03 | Otsuka Pharmaceutical Co., Ltd. | Oxindol compounds, compositions containing same and processes for preparing same |
| EP0219625A1 (en) * | 1985-10-15 | 1987-04-29 | Merrell Dow Pharmaceuticals Inc. | Cardiotonic heterocyclocarbonyl- and acetyl-thiazolones |
| GR890100646A (en) * | 1988-10-11 | 1990-11-29 | Conceils De Rech Soc D | Preparation process of new 2-mithoxycarbonyl substituted n,n-d1-(trimethoxybenzoyl) piperazines |
| BE1003518A3 (fr) * | 1988-10-11 | 1992-04-14 | Sod Conseils Rech Applic | Nouveaux derives de la methoxycarbonyl-2-n,n'-di-(trimethoxybenzoyle) piperazine, un procede pour leur preparation et compositions therapeutiques en contenant. |
| FR2637593A1 (fr) * | 1988-10-11 | 1990-04-13 | Scras | Nouveaux derives de la carbonyl-2 n,n(prime)-di-(trimethoxybenzoyle) piperazine, ainsi que leur procede de preparation |
| FR2637592A1 (fr) * | 1988-10-11 | 1990-04-13 | Scras | Nouveaux derives de la methoxycarbonyl-2 n,n(prime)-di-(trimethoxybenzoyle) piperazine, ainsi que leur procede de preparation |
| BE1003519A3 (fr) * | 1988-10-11 | 1992-04-14 | Scras | Nouveaux derives de la carbonyl-2 n,n'-di-(trimethoxybenzoyle) piperazine, un procede pour leur preparation et compositions therapeutiques en contenant. |
| GR890100647A (en) * | 1988-10-11 | 1990-11-29 | Conseils De Rech Soc D | 1,4-disubstituted piperazine compounds their production and use |
| FR2637499A1 (fr) * | 1988-10-11 | 1990-04-13 | Scras | Medicaments a base de nouveaux derives de la methoxycarbonyl-2 n, n'-di-(trimethoxybenzoyle) piperazine |
| FR2637500A1 (fr) * | 1988-10-11 | 1990-04-13 | Scras | Medicaments a base de nouveaux derives de la carbonyl-2 n, n'-di-(trimethoxybenzoyle) piperazine |
| GR900100270A (en) * | 1989-04-15 | 1991-09-27 | Conceils De Rech Soc D | Preparation method for 2-substituted n n-bitrimethoxybenzol-piperazines |
| FR2645743A1 (fr) * | 1989-04-15 | 1990-10-19 | Scras | Compositions therapeutiques a base de derives di-substitues des n,n(prime)-ditrimethoxybenzoyle piperazines |
| FR2645859A1 (fr) * | 1989-04-15 | 1990-10-19 | Scras | Derives di-substitues des n,n(prime)-ditrimethoxybenzoyle piperazines ainsi que leur procede de preparation |
| BE1007245A3 (fr) * | 1989-04-15 | 1995-05-02 | Sod Conseils Rech Applic | Derives di-substitues des n, n'-ditrimethoxybenzoyle piperazine, un procede pour leur preparation et compositions therapeutiques en contenant. |
| WO1996016052A3 (en) * | 1994-11-17 | 1996-08-01 | Molecular Geriatrics Corp | Certain substituted 1-aryl-3-piperazin-1'-yl propanones |
| US5693804A (en) * | 1994-11-17 | 1997-12-02 | Molecular Geriatrics Corporation | Substituted 1-aryl-3-piperazin-1'-yl propanones |
| US7173132B2 (en) | 1994-11-17 | 2007-02-06 | Molecular Geriatrics Corporation | Certain substituted 1-aryl-3-piperazine-1′-yl propanones |
| US6214994B1 (en) | 1997-04-21 | 2001-04-10 | Molecular Geriatrics Corporation | Certain substituted 1-aryl-3-piperazin-1′-yl propanones |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS4993334A (en, 2012) | 1974-09-05 |
| BE808337A (fr) | 1974-06-06 |
| FR2209560A1 (en) | 1974-07-05 |
| NL7316714A (en, 2012) | 1974-06-11 |
| ES421159A1 (es) | 1976-04-16 |
| DD109632A5 (en, 2012) | 1974-11-12 |
| ES421160A1 (es) | 1976-04-16 |
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