CH523245A - Verfahren zur Herstellung von neuen basischen Pyrrolderivaten - Google Patents
Verfahren zur Herstellung von neuen basischen PyrrolderivatenInfo
- Publication number
- CH523245A CH523245A CH616672A CH616672A CH523245A CH 523245 A CH523245 A CH 523245A CH 616672 A CH616672 A CH 616672A CH 616672 A CH616672 A CH 616672A CH 523245 A CH523245 A CH 523245A
- Authority
- CH
- Switzerland
- Prior art keywords
- phenyl
- acid
- general formula
- pyrrole
- aminoethyl
- Prior art date
Links
- PDANDSZHFPDMMU-UHFFFAOYSA-N 2-(4-pyrrol-1-ylphenyl)ethanamine Chemical class C1=CC(CCN)=CC=C1N1C=CC=C1 PDANDSZHFPDMMU-UHFFFAOYSA-N 0.000 title description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 7
- 238000000034 method Methods 0.000 claims abstract description 5
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 3
- 150000003839 salts Chemical class 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 11
- 150000003233 pyrroles Chemical class 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 6
- 150000002825 nitriles Chemical class 0.000 claims description 6
- 150000007522 mineralic acids Chemical class 0.000 claims description 5
- 150000007524 organic acids Chemical class 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 235000005985 organic acids Nutrition 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 230000003110 anti-inflammatory effect Effects 0.000 abstract description 3
- 230000001754 anti-pyretic effect Effects 0.000 abstract description 3
- 239000002221 antipyretic Substances 0.000 abstract description 2
- PCSMJKASWLYICJ-UHFFFAOYSA-N Succinic aldehyde Chemical compound O=CCCC=O PCSMJKASWLYICJ-UHFFFAOYSA-N 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- 239000000730 antalgic agent Substances 0.000 abstract 1
- 229940125716 antipyretic agent Drugs 0.000 abstract 1
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 abstract 1
- 125000000168 pyrrolyl group Chemical group 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 34
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 239000004480 active ingredient Substances 0.000 description 17
- 239000000243 solution Substances 0.000 description 17
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 239000002253 acid Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
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- 235000019322 gelatine Nutrition 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000000454 talc Substances 0.000 description 5
- 229910052623 talc Inorganic materials 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 108010010803 Gelatin Proteins 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
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- 235000011852 gelatine desserts Nutrition 0.000 description 4
- 235000019359 magnesium stearate Nutrition 0.000 description 4
- 239000000155 melt Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 229920001223 polyethylene glycol Polymers 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
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- 241000700159 Rattus Species 0.000 description 3
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 3
- 235000010323 ascorbic acid Nutrition 0.000 description 3
- 239000011668 ascorbic acid Substances 0.000 description 3
- 229960005070 ascorbic acid Drugs 0.000 description 3
- 239000002775 capsule Substances 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
- -1 cocoa butter) Chemical class 0.000 description 3
- 239000008120 corn starch Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- 229920001592 potato starch Polymers 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
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- 239000003381 stabilizer Substances 0.000 description 3
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- 239000000829 suppository Substances 0.000 description 3
- IZFIKCWNOXLCSJ-UHFFFAOYSA-N 2-(3-chloro-4-pyrrol-1-ylphenyl)acetonitrile Chemical compound ClC=1C=C(C=CC1N1C=CC=C1)CC#N IZFIKCWNOXLCSJ-UHFFFAOYSA-N 0.000 description 2
- COQVQUFCOZUAGT-UHFFFAOYSA-N 2-(3-chloro-4-pyrrol-1-ylphenyl)ethanamine Chemical compound NCCC1=CC(Cl)=C(C=C1)N1C=CC=C1 COQVQUFCOZUAGT-UHFFFAOYSA-N 0.000 description 2
- TUPNPKCVKSNDIU-UHFFFAOYSA-N 2-(4-pyrrol-1-ylphenyl)acetonitrile Chemical compound C1=CC(CC#N)=CC=C1N1C=CC=C1 TUPNPKCVKSNDIU-UHFFFAOYSA-N 0.000 description 2
- GAPNGRGLUYWSMI-UHFFFAOYSA-N 2-(4-pyrrol-1-ylphenyl)ethanamine hydrochloride Chemical compound Cl.NCCC1=CC=C(C=C1)N1C=CC=C1 GAPNGRGLUYWSMI-UHFFFAOYSA-N 0.000 description 2
- HBWHDLQIWGCMTA-UHFFFAOYSA-N 2-(4-pyrrol-1-ylphenyl)propan-1-amine Chemical compound NCC(C)C1=CC=C(C=C1)N1C=CC=C1 HBWHDLQIWGCMTA-UHFFFAOYSA-N 0.000 description 2
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 2
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
- 244000215068 Acacia senegal Species 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- 229920000084 Gum arabic Polymers 0.000 description 2
- 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 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000007868 Raney catalyst Substances 0.000 description 2
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
- 229910000564 Raney nickel Inorganic materials 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 239000000205 acacia gum Substances 0.000 description 2
- 235000010489 acacia gum Nutrition 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 239000003708 ampul Substances 0.000 description 2
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- 239000003054 catalyst Substances 0.000 description 2
- 229940110456 cocoa butter Drugs 0.000 description 2
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- 239000012153 distilled water Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 229940093915 gynecological organic acid Drugs 0.000 description 2
- 150000002431 hydrogen Chemical group 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
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- 238000003756 stirring Methods 0.000 description 2
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- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- DCXXMTOCNZCJGO-UHFFFAOYSA-N tristearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC DCXXMTOCNZCJGO-UHFFFAOYSA-N 0.000 description 2
- 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 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
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- 239000003791 organic solvent mixture Substances 0.000 description 1
- 239000003973 paint Substances 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
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000000552 rheumatic effect Effects 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- 239000004296 sodium metabisulphite Substances 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- 239000007901 soft capsule Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/325—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/325—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
- C07D207/327—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH616672A CH523245A (de) | 1969-10-17 | 1969-10-17 | Verfahren zur Herstellung von neuen basischen Pyrrolderivaten |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1554569A CH523883A (de) | 1969-10-17 | 1969-10-17 | Verfahren zur Herstellung von neuen basischen Pyrrolderivaten |
| CH616672A CH523245A (de) | 1969-10-17 | 1969-10-17 | Verfahren zur Herstellung von neuen basischen Pyrrolderivaten |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH523245A true CH523245A (de) | 1972-05-31 |
Family
ID=4409965
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH616672A CH523245A (de) | 1969-10-17 | 1969-10-17 | Verfahren zur Herstellung von neuen basischen Pyrrolderivaten |
| CH616772A CH523246A (de) | 1969-10-17 | 1969-10-17 | Verfahren zur Herstellung von neuen basischen Pyrrolderivaten |
| CH617072A CH523247A (de) | 1969-10-17 | 1969-10-17 | Verfahren zur Herstellung von neuen basischen Pyrrolderivaten |
| CH616572A CH523244A (de) | 1969-10-17 | 1969-10-17 | Verfahren zur Herstellung von neuen basischen Pyrrolderivaten |
Family Applications After (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH616772A CH523246A (de) | 1969-10-17 | 1969-10-17 | Verfahren zur Herstellung von neuen basischen Pyrrolderivaten |
| CH617072A CH523247A (de) | 1969-10-17 | 1969-10-17 | Verfahren zur Herstellung von neuen basischen Pyrrolderivaten |
| CH616572A CH523244A (de) | 1969-10-17 | 1969-10-17 | Verfahren zur Herstellung von neuen basischen Pyrrolderivaten |
Country Status (7)
| Country | Link |
|---|---|
| AU (1) | AU2117070A (enExample) |
| CA (1) | CA921037A (enExample) |
| CH (4) | CH523245A (enExample) |
| ES (9) | ES384599A1 (enExample) |
| IL (1) | IL35465A (enExample) |
| SU (3) | SU374823A3 (enExample) |
| ZA (1) | ZA707058B (enExample) |
-
1969
- 1969-10-17 CH CH616672A patent/CH523245A/de not_active IP Right Cessation
- 1969-10-17 CH CH616772A patent/CH523246A/de not_active IP Right Cessation
- 1969-10-17 CH CH617072A patent/CH523247A/de not_active IP Right Cessation
- 1969-10-17 CH CH616572A patent/CH523244A/de not_active IP Right Cessation
-
1970
- 1970-10-15 SU SU1487452A patent/SU374823A3/ru active
- 1970-10-15 SU SU1486890A patent/SU372812A3/ru active
- 1970-10-15 SU SU1486889A patent/SU368748A3/ru active
- 1970-10-16 CA CA095737A patent/CA921037A/en not_active Expired
- 1970-10-16 ES ES384599A patent/ES384599A1/es not_active Expired
- 1970-10-16 ES ES384605A patent/ES384605A1/es not_active Expired
- 1970-10-16 ES ES384598A patent/ES384598A1/es not_active Expired
- 1970-10-16 ES ES384597A patent/ES384597A1/es not_active Expired
- 1970-10-16 AU AU21170/70A patent/AU2117070A/en not_active Expired
- 1970-10-16 ES ES384602A patent/ES384602A1/es not_active Expired
- 1970-10-16 ES ES384604A patent/ES384604A1/es not_active Expired
- 1970-10-16 ES ES384603A patent/ES384603A1/es not_active Expired
- 1970-10-16 ES ES384600A patent/ES384600A1/es not_active Expired
- 1970-10-16 ES ES384601A patent/ES384601A1/es not_active Expired
- 1970-10-16 ZA ZA707058A patent/ZA707058B/xx unknown
- 1970-10-16 IL IL35465A patent/IL35465A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES384598A1 (es) | 1973-01-16 |
| ES384600A1 (es) | 1973-01-16 |
| ES384597A1 (es) | 1973-01-16 |
| ES384601A1 (es) | 1973-01-16 |
| SU368748A3 (enExample) | 1973-01-26 |
| SU372812A3 (enExample) | 1973-03-01 |
| CH523247A (de) | 1972-05-31 |
| ZA707058B (en) | 1971-09-29 |
| ES384605A1 (es) | 1973-01-16 |
| AU2117070A (en) | 1973-04-20 |
| ES384599A1 (es) | 1973-01-16 |
| CH523246A (de) | 1972-05-31 |
| SU374823A3 (enExample) | 1973-03-20 |
| IL35465A (en) | 1972-10-29 |
| ES384603A1 (es) | 1973-01-16 |
| IL35465A0 (en) | 1970-12-24 |
| ES384602A1 (es) | 1973-01-16 |
| CA921037A (en) | 1973-02-13 |
| ES384604A1 (es) | 1973-01-16 |
| CH523244A (de) | 1972-05-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |