CH503726A - Verfahren zur Herstellung von neuen Estern substituierter Phenylessigsäuren - Google Patents
Verfahren zur Herstellung von neuen Estern substituierter PhenylessigsäurenInfo
- Publication number
- CH503726A CH503726A CH1641170A CH1641170A CH503726A CH 503726 A CH503726 A CH 503726A CH 1641170 A CH1641170 A CH 1641170A CH 1641170 A CH1641170 A CH 1641170A CH 503726 A CH503726 A CH 503726A
- Authority
- CH
- Switzerland
- Prior art keywords
- phenyl
- pyrryl
- acid
- general formula
- solution
- Prior art date
Links
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical class OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 title claims description 9
- 230000000202 analgesic effect Effects 0.000 title description 3
- -1 polymethyleneimino residue Polymers 0.000 claims abstract description 20
- 150000003839 salts Chemical class 0.000 claims abstract description 19
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 4
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims abstract description 3
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 76
- 239000002253 acid Substances 0.000 claims description 20
- 150000002148 esters Chemical class 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 9
- 150000007522 mineralic acids Chemical class 0.000 claims description 6
- 150000007524 organic acids Chemical class 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract description 60
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 abstract description 5
- 229910052801 chlorine Inorganic materials 0.000 abstract description 2
- 229910052731 fluorine Inorganic materials 0.000 abstract description 2
- WNRWEBKEQARBKV-UHFFFAOYSA-N 1-(2-chloroethyl)piperidine Chemical compound ClCCN1CCCCC1 WNRWEBKEQARBKV-UHFFFAOYSA-N 0.000 abstract 1
- 229940035676 analgesics Drugs 0.000 abstract 1
- 239000000730 antalgic agent Substances 0.000 abstract 1
- 230000001741 anti-phlogistic effect Effects 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 84
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 66
- 239000000243 solution Substances 0.000 description 54
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 45
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 239000011541 reaction mixture Substances 0.000 description 21
- 239000000203 mixture Substances 0.000 description 20
- 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 18
- 239000011734 sodium Substances 0.000 description 18
- 229910052708 sodium Inorganic materials 0.000 description 18
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 17
- 239000003921 oil Substances 0.000 description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 14
- 239000000155 melt Substances 0.000 description 14
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 13
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 12
- 238000009835 boiling Methods 0.000 description 11
- KLABMFIJWMBVMC-UHFFFAOYSA-N ethyl 2-(4-pyrrol-1-ylphenyl)acetate Chemical compound C(C)OC(CC1=CC=C(C=C1)N1C=CC=C1)=O KLABMFIJWMBVMC-UHFFFAOYSA-N 0.000 description 10
- 238000010992 reflux Methods 0.000 description 10
- REEGEVWKFIVCQX-UHFFFAOYSA-N 2-(4-pyrrol-1-ylphenyl)butanoic acid Chemical compound N1(C=CC=C1)C1=CC=C(C=C1)C(C(=O)O)CC REEGEVWKFIVCQX-UHFFFAOYSA-N 0.000 description 9
- 229960000583 acetic acid Drugs 0.000 description 9
- 238000002844 melting Methods 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- 238000001953 recrystallisation Methods 0.000 description 9
- 239000007858 starting material Substances 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- 238000001704 evaporation Methods 0.000 description 8
- 230000008020 evaporation Effects 0.000 description 8
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 8
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 8
- 239000013078 crystal Substances 0.000 description 7
- 239000005457 ice water Substances 0.000 description 7
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 7
- 235000019341 magnesium sulphate Nutrition 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 6
- 239000012362 glacial acetic acid Substances 0.000 description 6
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 6
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- NCXUNZWLEYGQAH-UHFFFAOYSA-N 1-(dimethylamino)propan-2-ol Chemical compound CC(O)CN(C)C NCXUNZWLEYGQAH-UHFFFAOYSA-N 0.000 description 5
- ANAQSKGWPSBAPF-UHFFFAOYSA-N 2-(3-chloro-4-pyrrol-1-ylphenyl)propanoic acid Chemical compound ClC1=CC(C(C(O)=O)C)=CC=C1N1C=CC=C1 ANAQSKGWPSBAPF-UHFFFAOYSA-N 0.000 description 5
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 5
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 5
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 5
- 125000005907 alkyl ester group Chemical group 0.000 description 5
- DBAYAOOQJWDHLM-UHFFFAOYSA-N methyl 2-(4-pyrrol-1-ylphenyl)butanoate Chemical compound COC(C(CC)C1=CC=C(C=C1)N1C=CC=C1)=O DBAYAOOQJWDHLM-UHFFFAOYSA-N 0.000 description 5
- 235000015497 potassium bicarbonate Nutrition 0.000 description 5
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 5
- 239000011736 potassium bicarbonate Substances 0.000 description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 5
- GFISDBXSWQMOND-UHFFFAOYSA-N 2,5-dimethoxyoxolane Chemical compound COC1CCC(OC)O1 GFISDBXSWQMOND-UHFFFAOYSA-N 0.000 description 4
- KCZGWRZYJZGMQW-UHFFFAOYSA-N 2-(4-pyrrol-1-ylphenyl)acetic acid Chemical compound C1=CC(CC(=O)O)=CC=C1N1C=CC=C1 KCZGWRZYJZGMQW-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 235000019439 ethyl acetate Nutrition 0.000 description 4
- 125000004494 ethyl ester group Chemical group 0.000 description 4
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 4
- 235000011118 potassium hydroxide Nutrition 0.000 description 4
- BOTYEUNQFXTDNF-UHFFFAOYSA-N 2-(3-chloro-4-pyrrol-1-ylphenyl)butanoic acid Chemical compound ClC=1C=C(C=CC1N1C=CC=C1)C(C(=O)O)CC BOTYEUNQFXTDNF-UHFFFAOYSA-N 0.000 description 3
- BZSXEZOLBIJVQK-UHFFFAOYSA-N 2-methylsulfonylbenzoic acid Chemical compound CS(=O)(=O)C1=CC=CC=C1C(O)=O BZSXEZOLBIJVQK-UHFFFAOYSA-N 0.000 description 3
- PYSGFFTXMUWEOT-UHFFFAOYSA-N 3-(dimethylamino)propan-1-ol Chemical compound CN(C)CCCO PYSGFFTXMUWEOT-UHFFFAOYSA-N 0.000 description 3
- GNXPCFWROFHBQI-UHFFFAOYSA-N C(C)OC(C(C)C1=CC=C(C=C1)N1C=CC=C1)=O Chemical compound C(C)OC(C(C)C1=CC=C(C=C1)N1C=CC=C1)=O GNXPCFWROFHBQI-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- WIRUZQNBHNAMAB-UHFFFAOYSA-N benzene;cyclohexane Chemical compound C1CCCCC1.C1=CC=CC=C1 WIRUZQNBHNAMAB-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- QSKWJTXWJJOJFP-UHFFFAOYSA-N chloroform;ethoxyethane Chemical compound ClC(Cl)Cl.CCOCC QSKWJTXWJJOJFP-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
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 3
- MPNLEQFETFHVJG-UHFFFAOYSA-N ethyl 2-(3-chloro-4-pyrrol-1-ylphenyl)propanoate Chemical compound C(C)OC(C(C)C1=CC(=C(C=C1)N1C=CC=C1)Cl)=O MPNLEQFETFHVJG-UHFFFAOYSA-N 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 229940050411 fumarate Drugs 0.000 description 3
- 229940093915 gynecological organic acid Drugs 0.000 description 3
- 235000005985 organic acids Nutrition 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- OUWZQVMCWOTSJN-UHFFFAOYSA-N 1-(dimethylamino)propan-2-yl 2-(4-pyrrol-1-ylphenyl)acetate Chemical compound CN(CC(C)OC(CC1=CC=C(C=C1)N1C=CC=C1)=O)C OUWZQVMCWOTSJN-UHFFFAOYSA-N 0.000 description 2
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 2
- APKGOXFOTBQTLW-UHFFFAOYSA-N 2-(4-amino-3-chlorophenyl)butanoic acid Chemical compound CCC(C(O)=O)C1=CC=C(N)C(Cl)=C1 APKGOXFOTBQTLW-UHFFFAOYSA-N 0.000 description 2
- WAPLXGPARWRGJO-UHFFFAOYSA-N 2-(4-aminophenyl)butanoic acid Chemical compound CCC(C(O)=O)C1=CC=C(N)C=C1 WAPLXGPARWRGJO-UHFFFAOYSA-N 0.000 description 2
- BWCOHXICZCDKPF-UHFFFAOYSA-N 2-(4-pyrrol-1-ylphenyl)propanoic acid Chemical compound C1=CC(C(C(O)=O)C)=CC=C1N1C=CC=C1 BWCOHXICZCDKPF-UHFFFAOYSA-N 0.000 description 2
- IWSZDQRGNFLMJS-UHFFFAOYSA-N 2-(dibutylamino)ethanol Chemical compound CCCCN(CCO)CCCC IWSZDQRGNFLMJS-UHFFFAOYSA-N 0.000 description 2
- INUAENHGGDSXIG-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-(4-pyrrol-1-ylphenyl)butanoate Chemical compound CN(CCOC(C(CC)C1=CC=C(C=C1)N1C=CC=C1)=O)C INUAENHGGDSXIG-UHFFFAOYSA-N 0.000 description 2
- KZTWONRVIPPDKH-UHFFFAOYSA-N 2-(piperidin-1-yl)ethanol Chemical compound OCCN1CCCCC1 KZTWONRVIPPDKH-UHFFFAOYSA-N 0.000 description 2
- XWKFPIODWVPXLX-UHFFFAOYSA-N 2-methyl-5-methylpyridine Natural products CC1=CC=C(C)N=C1 XWKFPIODWVPXLX-UHFFFAOYSA-N 0.000 description 2
- QLRFZIMSGIYEFP-UHFFFAOYSA-N 2-pyrrolidin-1-ylethyl 2-(4-pyrrol-1-ylphenyl)acetate Chemical compound O=C(CC1=CC=C(C=C1)N1C=CC=C1)OCCN1CCCC1 QLRFZIMSGIYEFP-UHFFFAOYSA-N 0.000 description 2
- MROJXXOCABQVEF-UHFFFAOYSA-N Actarit Chemical compound CC(=O)NC1=CC=C(CC(O)=O)C=C1 MROJXXOCABQVEF-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical class OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000001414 amino alcohols Chemical class 0.000 description 2
- 230000003110 anti-inflammatory effect Effects 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- 239000000812 cholinergic antagonist Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- CJMIDDHSNOTHGV-UHFFFAOYSA-N diethyl 2-(3-chloro-4-pyrrol-1-ylphenyl)-2-methylpropanedioate Chemical compound C(C)OC(C(C(=O)OCC)(C)C1=CC(=C(C=C1)N1C=CC=C1)Cl)=O CJMIDDHSNOTHGV-UHFFFAOYSA-N 0.000 description 2
- OOMAKVRRCRCMPH-UHFFFAOYSA-N diethyl 2-(3-chloro-4-pyrrol-1-ylphenyl)propanedioate Chemical compound C(C)OC(C(C(=O)OCC)C1=CC(=C(C=C1)N1C=CC=C1)Cl)=O OOMAKVRRCRCMPH-UHFFFAOYSA-N 0.000 description 2
- FIVOVHXWYYCDSX-UHFFFAOYSA-N diethyl 2-(4-pyrrol-1-ylphenyl)propanedioate Chemical compound C(C)OC(C(C(=O)OCC)C1=CC=C(C=C1)N1C=CC=C1)=O FIVOVHXWYYCDSX-UHFFFAOYSA-N 0.000 description 2
- DVGWSFWVOHHOJS-UHFFFAOYSA-N diethyl 2-methyl-2-(4-pyrrol-1-ylphenyl)propanedioate Chemical compound CCOC(=O)C(C)(C(=O)OCC)C1=CC=C(C=C1)N1C=CC=C1 DVGWSFWVOHHOJS-UHFFFAOYSA-N 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- NHGYQADUGSHIGS-UHFFFAOYSA-N ethyl 2-(4-amino-3-chlorophenyl)acetate Chemical compound CCOC(=O)CC1=CC=C(N)C(Cl)=C1 NHGYQADUGSHIGS-UHFFFAOYSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- XQYZDYMELSJDRZ-UHFFFAOYSA-N papaverine Chemical compound C1=C(OC)C(OC)=CC=C1CC1=NC=CC2=CC(OC)=C(OC)C=C12 XQYZDYMELSJDRZ-UHFFFAOYSA-N 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 239000003279 phenylacetic acid Substances 0.000 description 2
- 229960003424 phenylacetic acid Drugs 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-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
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 2
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 1
- AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 1
- UCMFZAZGBPYDAD-UHFFFAOYSA-N 2-(3-chloro-4-pyrrol-1-ylphenyl)acetic acid Chemical compound ClC=1C=C(C=CC1N1C=CC=C1)CC(=O)O UCMFZAZGBPYDAD-UHFFFAOYSA-N 0.000 description 1
- ODICNAMBOUGNAW-UHFFFAOYSA-N 2-(4-acetamidophenyl)butanoic acid Chemical compound C(C)(=O)NC1=CC=C(C=C1)C(C(=O)O)CC ODICNAMBOUGNAW-UHFFFAOYSA-N 0.000 description 1
- RNPFHSPLVUBKAU-UHFFFAOYSA-N 2-(4-amino-3-chlorophenyl)acetic acid Chemical compound NC1=CC=C(CC(O)=O)C=C1Cl RNPFHSPLVUBKAU-UHFFFAOYSA-N 0.000 description 1
- QFHUAUCQDSNKRL-UHFFFAOYSA-N 2-(4-pyrrol-1-ylphenyl)butanoyl chloride Chemical compound N1(C=CC=C1)C1=CC=C(C=C1)C(C(=O)Cl)CC QFHUAUCQDSNKRL-UHFFFAOYSA-N 0.000 description 1
- ALMZGLXCPLKLMU-UHFFFAOYSA-N 2-(dibutylamino)ethyl 2-(4-pyrrol-1-ylphenyl)acetate Chemical compound C(CCC)N(CCOC(CC1=CC=C(C=C1)N1C=CC=C1)=O)CCCC ALMZGLXCPLKLMU-UHFFFAOYSA-N 0.000 description 1
- QDTNVEPSFWAUGO-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-(3-chloro-4-pyrrol-1-ylphenyl)acetate Chemical compound CN(CCOC(CC1=CC(=C(C=C1)N1C=CC=C1)Cl)=O)C QDTNVEPSFWAUGO-UHFFFAOYSA-N 0.000 description 1
- KSFCSWBXBBTOQK-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-(4-pyrrol-1-ylphenyl)acetate Chemical compound CN(CCOC(CC1=CC=C(C=C1)N1C=CC=C1)=O)C KSFCSWBXBBTOQK-UHFFFAOYSA-N 0.000 description 1
- KKFDCBRMNNSAAW-UHFFFAOYSA-N 2-(morpholin-4-yl)ethanol Chemical compound OCCN1CCOCC1 KKFDCBRMNNSAAW-UHFFFAOYSA-N 0.000 description 1
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 1
- QRNOIPGHNOJGMJ-UHFFFAOYSA-N 2-morpholin-4-ylethyl 2-(4-pyrrol-1-ylphenyl)acetate Chemical compound O1CCN(CC1)CCOC(CC1=CC=C(C=C1)N1C=CC=C1)=O QRNOIPGHNOJGMJ-UHFFFAOYSA-N 0.000 description 1
- RLQZIECDMISZHS-UHFFFAOYSA-N 2-phenylcyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C=CC(=O)C(C=2C=CC=CC=2)=C1 RLQZIECDMISZHS-UHFFFAOYSA-N 0.000 description 1
- MZGDUKXOSPYARN-UHFFFAOYSA-N 2-piperidin-1-ylethyl 2-(4-pyrrol-1-ylphenyl)butanoate Chemical compound N1(CCCCC1)CCOC(C(CC)C1=CC=C(C=C1)N1C=CC=C1)=O MZGDUKXOSPYARN-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
- 229930008281 A03AD01 - Papaverine Natural products 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
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- JEYSHNQIUIHGKF-UHFFFAOYSA-N CN(C)CCC(C(O)=O)C(C=C1)=CC=C1N1C=CC=C1 Chemical compound CN(C)CCC(C(O)=O)C(C=C1)=CC=C1N1C=CC=C1 JEYSHNQIUIHGKF-UHFFFAOYSA-N 0.000 description 1
- 241000700199 Cavia porcellus Species 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 238000000023 Kugelrohr distillation Methods 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 206010030113 Oedema Diseases 0.000 description 1
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- 208000025747 Rheumatic disease Diseases 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- PCSMJKASWLYICJ-UHFFFAOYSA-N Succinic aldehyde Chemical compound O=CCCC=O PCSMJKASWLYICJ-UHFFFAOYSA-N 0.000 description 1
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- AZVVWEVZHVKBTP-UHFFFAOYSA-N acetic acid;naphthalene-1,5-disulfonic acid Chemical compound CC(O)=O.C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1S(O)(=O)=O AZVVWEVZHVKBTP-UHFFFAOYSA-N 0.000 description 1
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- 239000000654 additive Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- HOPRXXXSABQWAV-UHFFFAOYSA-N anhydrous collidine Natural products CC1=CC=NC(C)=C1C HOPRXXXSABQWAV-UHFFFAOYSA-N 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 229940124599 anti-inflammatory drug Drugs 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- WDIHJSXYQDMJHN-UHFFFAOYSA-L barium chloride Chemical compound [Cl-].[Cl-].[Ba+2] WDIHJSXYQDMJHN-UHFFFAOYSA-L 0.000 description 1
- 229910001626 barium chloride Inorganic materials 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- WPUJEWVVTKLMQI-UHFFFAOYSA-N benzene;ethoxyethane Chemical compound CCOCC.C1=CC=CC=C1 WPUJEWVVTKLMQI-UHFFFAOYSA-N 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 229960004365 benzoic acid Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 229960004106 citric acid Drugs 0.000 description 1
- UTBIMNXEDGNJFE-UHFFFAOYSA-N collidine Natural products CC1=CC=C(C)C(C)=N1 UTBIMNXEDGNJFE-UHFFFAOYSA-N 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 238000004042 decolorization Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- XBRDBODLCHKXHI-UHFFFAOYSA-N epolamine Chemical compound OCCN1CCCC1 XBRDBODLCHKXHI-UHFFFAOYSA-N 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-N ethanesulfonic acid Chemical compound CCS(O)(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-N 0.000 description 1
- XTLNYNMNUCLWEZ-UHFFFAOYSA-N ethanol;propan-2-one Chemical compound CCO.CC(C)=O XTLNYNMNUCLWEZ-UHFFFAOYSA-N 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- YKWNUSJLICDQEO-UHFFFAOYSA-N ethoxyethane;propan-2-ol Chemical compound CC(C)O.CCOCC YKWNUSJLICDQEO-UHFFFAOYSA-N 0.000 description 1
- DJNMOHZQUVIZMS-UHFFFAOYSA-N ethyl 2-(3-chloro-4-pyrrol-1-ylphenyl)acetate Chemical compound C(C)OC(CC1=CC(=C(C=C1)N1C=CC=C1)Cl)=O DJNMOHZQUVIZMS-UHFFFAOYSA-N 0.000 description 1
- OWYIIYUIZFXFDM-UHFFFAOYSA-N ethyl 2-(3-chloro-4-pyrrol-1-ylphenyl)butanoate Chemical compound C(C)OC(C(CC)C1=CC(=C(C=C1)N1C=CC=C1)Cl)=O OWYIIYUIZFXFDM-UHFFFAOYSA-N 0.000 description 1
- WVDXMTOPOKZMOM-UHFFFAOYSA-N ethyl 2-(4-pyrrol-1-ylphenyl)butanoate Chemical compound CCOC(=O)C(CC)C1=CC=C(C=C1)N1C=CC=C1 WVDXMTOPOKZMOM-UHFFFAOYSA-N 0.000 description 1
- ANFZRGMDGDYNGA-UHFFFAOYSA-N ethyl acetate;propan-2-ol Chemical compound CC(C)O.CCOC(C)=O ANFZRGMDGDYNGA-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 235000011087 fumaric acid Nutrition 0.000 description 1
- 229960002598 fumaric acid Drugs 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 238000003306 harvesting Methods 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 208000027866 inflammatory disease Diseases 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 229960000448 lactic acid Drugs 0.000 description 1
- 230000002101 lytic effect Effects 0.000 description 1
- 238000003760 magnetic stirring Methods 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 229940098895 maleic acid Drugs 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 229940099690 malic acid Drugs 0.000 description 1
- 150000002691 malonic acids Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- DGEYTDCFMQMLTH-UHFFFAOYSA-N methanol;propan-2-ol Chemical compound OC.CC(C)O DGEYTDCFMQMLTH-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000007530 organic bases Chemical group 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
- 229960001789 papaverine Drugs 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 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 description 1
- 229940072033 potash Drugs 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 229960005335 propanol Drugs 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000000552 rheumatic effect Effects 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 150000003388 sodium compounds Chemical class 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- FIAFUQMPZJWCLV-UHFFFAOYSA-N suramin Chemical compound OS(=O)(=O)C1=CC(S(O)(=O)=O)=C2C(NC(=O)C3=CC=C(C(=C3)NC(=O)C=3C=C(NC(=O)NC=4C=C(C=CC=4)C(=O)NC=4C(=CC=C(C=4)C(=O)NC=4C5=C(C=C(C=C5C(=CC=4)S(O)(=O)=O)S(O)(=O)=O)S(O)(=O)=O)C)C=CC=3)C)=CC=C(S(O)(=O)=O)C2=C1 FIAFUQMPZJWCLV-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 229960001367 tartaric acid Drugs 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000005406 washing 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
- 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
-
- 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
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Pyrrole Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1641170A CH503726A (de) | 1968-04-29 | 1968-04-29 | Verfahren zur Herstellung von neuen Estern substituierter Phenylessigsäuren |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH637768A CH502334A (de) | 1968-04-29 | 1968-04-29 | Verfahren zur Herstellung von neuen Estern substituierter Phenylessigsäuren |
| CH1641170A CH503726A (de) | 1968-04-29 | 1968-04-29 | Verfahren zur Herstellung von neuen Estern substituierter Phenylessigsäuren |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH503726A true CH503726A (de) | 1971-02-28 |
Family
ID=4308611
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1641170A CH503726A (de) | 1968-04-29 | 1968-04-29 | Verfahren zur Herstellung von neuen Estern substituierter Phenylessigsäuren |
| CH1641270A CH502336A (de) | 1968-04-29 | 1968-04-29 | Verfahren zur Herstellung von neuen Estern substituierter Phenylessigsäuren |
| CH637768A CH502334A (de) | 1968-04-29 | 1968-04-29 | Verfahren zur Herstellung von neuen Estern substituierter Phenylessigsäuren |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1641270A CH502336A (de) | 1968-04-29 | 1968-04-29 | Verfahren zur Herstellung von neuen Estern substituierter Phenylessigsäuren |
| CH637768A CH502334A (de) | 1968-04-29 | 1968-04-29 | Verfahren zur Herstellung von neuen Estern substituierter Phenylessigsäuren |
Country Status (16)
| Country | Link |
|---|---|
| US (2) | US3697460A (OSRAM) |
| AT (2) | AT290521B (OSRAM) |
| BE (1) | BE732235A (OSRAM) |
| BG (3) | BG15550A3 (OSRAM) |
| BR (1) | BR6908404D0 (OSRAM) |
| CH (3) | CH503726A (OSRAM) |
| DE (1) | DE1921652A1 (OSRAM) |
| DK (1) | DK125591B (OSRAM) |
| ES (2) | ES366535A1 (OSRAM) |
| FR (1) | FR2007553A1 (OSRAM) |
| GB (1) | GB1263782A (OSRAM) |
| IL (1) | IL32084A (OSRAM) |
| NL (1) | NL6906207A (OSRAM) |
| NO (1) | NO127005B (OSRAM) |
| PL (1) | PL69820B1 (OSRAM) |
| SE (1) | SE342621B (OSRAM) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5682051B2 (ja) | 2006-05-18 | 2015-03-11 | ファーマサイクリックス，インク． | 細胞内キナーゼ阻害剤 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2986564A (en) * | 1959-02-20 | 1961-05-30 | Rips Richard | Pyrrole compounds |
-
1968
- 1968-04-29 CH CH1641170A patent/CH503726A/de not_active IP Right Cessation
- 1968-04-29 CH CH1641270A patent/CH502336A/de not_active IP Right Cessation
- 1968-04-29 CH CH637768A patent/CH502334A/de not_active IP Right Cessation
-
1969
- 1969-04-22 DK DK219669AA patent/DK125591B/da unknown
- 1969-04-22 SE SE5682/69A patent/SE342621B/xx unknown
- 1969-04-22 NO NO691668A patent/NO127005B/no unknown
- 1969-04-22 US US818408A patent/US3697460A/en not_active Expired - Lifetime
- 1969-04-22 NL NL6906207A patent/NL6906207A/xx unknown
- 1969-04-28 DE DE19691921652 patent/DE1921652A1/de active Pending
- 1969-04-28 IL IL32084A patent/IL32084A/xx unknown
- 1969-04-28 GB GB21519/69A patent/GB1263782A/en not_active Expired
- 1969-04-28 ES ES366535A patent/ES366535A1/es not_active Expired
- 1969-04-28 AT AT189470A patent/AT290521B/de not_active IP Right Cessation
- 1969-04-28 PL PL1969133263A patent/PL69820B1/pl unknown
- 1969-04-28 AT AT408869A patent/AT286975B/de not_active IP Right Cessation
- 1969-04-28 ES ES366536A patent/ES366536A1/es not_active Expired
- 1969-04-28 BG BG012133A patent/BG15550A3/bg unknown
- 1969-04-28 BR BR208404/69A patent/BR6908404D0/pt unknown
- 1969-04-28 BE BE732235D patent/BE732235A/xx unknown
- 1969-04-28 BG BG013143A patent/BG15388A3/bg unknown
- 1969-04-29 FR FR6913600A patent/FR2007553A1/fr not_active Withdrawn
- 1969-10-07 BG BG013142A patent/BG15209A3/bg unknown
-
1971
- 1971-09-22 US US00182855A patent/US3767802A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| IL32084A0 (en) | 1969-06-25 |
| FR2007553A1 (OSRAM) | 1970-01-09 |
| CH502334A (de) | 1971-01-31 |
| AT290521B (de) | 1971-06-11 |
| CH502336A (de) | 1971-01-31 |
| BG15209A3 (bg) | 1975-10-15 |
| AT286975B (de) | 1971-01-11 |
| ES366535A1 (es) | 1971-01-01 |
| IL32084A (en) | 1973-01-30 |
| SE342621B (OSRAM) | 1972-02-14 |
| BG15388A3 (bg) | 1976-05-10 |
| ES366536A1 (es) | 1971-01-01 |
| DK125591B (da) | 1973-03-12 |
| GB1263782A (en) | 1972-02-16 |
| PL69820B1 (OSRAM) | 1973-10-31 |
| BG15550A3 (bg) | 1972-05-20 |
| NO127005B (OSRAM) | 1973-04-24 |
| US3697460A (en) | 1972-10-10 |
| NL6906207A (OSRAM) | 1969-10-31 |
| BE732235A (OSRAM) | 1969-10-28 |
| US3767802A (en) | 1973-10-23 |
| BR6908404D0 (pt) | 1973-01-11 |
| DE1921652A1 (de) | 1969-11-13 |
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