CA1055951A - Process for preparing 1-ethyl-2-/2'-methoxy-5'-sulphonamidobenzoyl/-aminomethylpyrrolidine and its salts - Google Patents

Process for preparing 1-ethyl-2-/2'-methoxy-5'-sulphonamidobenzoyl/-aminomethylpyrrolidine and its salts

Info

Publication number: CA1055951A
Authority: CA; Canada
Prior art keywords: acid; ethyl; formula; chloro; pyrrolidine
Prior art date: 1975-03-28
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.): Expired

Application number

CA248,976A

Other languages

English (en)

French (fr)

Inventor

Judit Kosary

Gyorgy Somogyi

Endre Kasztreiner

Erno Orban

Lajos Farkas

Janos Borvendeg

Erzsebet Bursics

Eva Koczka

Tibor Balogh

Judit Eggenhofer

Veronika Pap

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Alkaloida Chemical Co Zrt

Original Assignee

Alkaloida Chemical Co Zrt

Priority date (The priority date 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 date listed.)

1975-03-28

Filing date

1976-03-26

Publication date

1979-06-05

1976-03-26 Application filed by Alkaloida Chemical Co Zrt filed Critical Alkaloida Chemical Co Zrt

1979-06-05 Application granted granted Critical

1979-06-05 Publication of CA1055951A publication Critical patent/CA1055951A/en

Status Expired legal-status Critical Current

Links

150000003839 salts Chemical class 0.000 title claims abstract description 11
238000004519 manufacturing process Methods 0.000 title claims description 4
239000002253 acid Substances 0.000 claims abstract description 46
150000001875 compounds Chemical class 0.000 claims abstract description 38
UNRBEYYLYRXYCG-UHFFFAOYSA-N (1-ethylpyrrolidin-2-yl)methanamine Chemical compound CCN1CCCC1CN UNRBEYYLYRXYCG-UHFFFAOYSA-N 0.000 claims abstract description 14
NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 claims abstract description 9
229910052751 metal Inorganic materials 0.000 claims abstract description 8
239000002184 metal Substances 0.000 claims abstract description 8
150000001408 amides Chemical class 0.000 claims abstract description 6
238000000034 method Methods 0.000 claims description 35
238000006243 chemical reaction Methods 0.000 claims description 26
230000008569 process Effects 0.000 claims description 12
239000002904 solvent Substances 0.000 claims description 12
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 9
150000002148 esters Chemical class 0.000 claims description 9
-1 alkali metal methoxide Chemical class 0.000 claims description 5
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 4
239000000654 additive Substances 0.000 claims description 2
230000000996 additive effect Effects 0.000 claims description 2
230000007935 neutral effect Effects 0.000 claims description 2
150000008065 acid anhydrides Chemical class 0.000 claims 1
125000001931 aliphatic group Chemical group 0.000 claims 1
229910052783 alkali metal Inorganic materials 0.000 claims 1
208000007107 Stomach Ulcer Diseases 0.000 abstract description 2
201000005917 gastric ulcer Diseases 0.000 abstract description 2
230000002401 inhibitory effect Effects 0.000 abstract description 2
230000000506 psychotropic effect Effects 0.000 abstract description 2
235000013350 formula milk Nutrition 0.000 description 40
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 23
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 22
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 20
239000000203 mixture Substances 0.000 description 20
239000002244 precipitate Substances 0.000 description 19
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
239000000243 solution Substances 0.000 description 18
238000002360 preparation method Methods 0.000 description 11
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 10
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 10
DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 10
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 10
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 9
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
229910052801 chlorine Inorganic materials 0.000 description 8
125000001309 chloro group Chemical group Cl* 0.000 description 8
238000001953 recrystallisation Methods 0.000 description 8
239000000126 substance Substances 0.000 description 8
XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 8
IKCLCGXPQILATA-UHFFFAOYSA-N 2-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1Cl IKCLCGXPQILATA-UHFFFAOYSA-N 0.000 description 7
CLHNTBSDCJLCKV-UHFFFAOYSA-N 2-chloro-5-chlorosulfonylbenzoic acid Chemical compound OC(=O)C1=CC(S(Cl)(=O)=O)=CC=C1Cl CLHNTBSDCJLCKV-UHFFFAOYSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
238000007792 addition Methods 0.000 description 6
239000002585 base Substances 0.000 description 6
235000011167 hydrochloric acid Nutrition 0.000 description 6
229960000443 hydrochloric acid Drugs 0.000 description 6
238000003756 stirring Methods 0.000 description 6
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 5
238000001816 cooling Methods 0.000 description 5
238000010438 heat treatment Methods 0.000 description 5
239000005457 ice water Substances 0.000 description 5
238000002844 melting Methods 0.000 description 5
230000008018 melting Effects 0.000 description 5
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 5
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 5
150000007513 acids Chemical class 0.000 description 4
229910021529 ammonia Inorganic materials 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
125000004494 ethyl ester group Chemical group 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
239000001117 sulphuric acid Substances 0.000 description 4
235000011149 sulphuric acid Nutrition 0.000 description 4
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 3
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 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-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
150000001540 azides Chemical class 0.000 description 3
230000008901 benefit Effects 0.000 description 3
238000009835 boiling Methods 0.000 description 3
239000006227 byproduct Substances 0.000 description 3
230000008859 change Effects 0.000 description 3
239000003610 charcoal Substances 0.000 description 3
239000007795 chemical reaction product Substances 0.000 description 3
229940093476 ethylene glycol Drugs 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
239000000047 product Substances 0.000 description 3
238000000746 purification Methods 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
238000010992 reflux Methods 0.000 description 3
239000011734 sodium Substances 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 2
BGRJTUBHPOOWDU-NSHDSACASA-N (S)-(-)-sulpiride Chemical compound CCN1CCC[C@H]1CNC(=O)C1=CC(S(N)(=O)=O)=CC=C1OC BGRJTUBHPOOWDU-NSHDSACASA-N 0.000 description 2
ONQBOTKLCMXPOF-UHFFFAOYSA-N 1-ethylpyrrolidine Chemical group CCN1CCCC1 ONQBOTKLCMXPOF-UHFFFAOYSA-N 0.000 description 2
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
ILUJQPXNXACGAN-UHFFFAOYSA-N O-methylsalicylic acid Chemical compound COC1=CC=CC=C1C(O)=O ILUJQPXNXACGAN-UHFFFAOYSA-N 0.000 description 2
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
239000000908 ammonium hydroxide Substances 0.000 description 2
125000004429 atom Chemical group 0.000 description 2
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
230000006866 deterioration Effects 0.000 description 2
238000005886 esterification reaction Methods 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
239000007789 gas Substances 0.000 description 2
150000004820 halides Chemical class 0.000 description 2
125000005843 halogen group Chemical group 0.000 description 2
230000003993 interaction Effects 0.000 description 2
150000004702 methyl esters Chemical class 0.000 description 2
239000012452 mother liquor Substances 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
125000004433 nitrogen atom Chemical group N* 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
229910052698 phosphorus Inorganic materials 0.000 description 2
239000011574 phosphorus Substances 0.000 description 2
239000000843 powder Substances 0.000 description 2
YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
229960004940 sulpiride Drugs 0.000 description 2
150000003512 tertiary amines Chemical group 0.000 description 2
NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
JDIIGWSSTNUWGK-UHFFFAOYSA-N 1h-imidazol-3-ium;chloride Chemical compound [Cl-].[NH2+]1C=CN=C1 JDIIGWSSTNUWGK-UHFFFAOYSA-N 0.000 description 1
FWWOWPGPERBCNJ-UHFFFAOYSA-N 2-hydroxy-4-(2-hydroxyethoxy)-4-oxobutanoic acid Chemical compound OCCOC(=O)CC(O)C(O)=O FWWOWPGPERBCNJ-UHFFFAOYSA-N 0.000 description 1
CFBYEGUGFPZCNF-UHFFFAOYSA-N 2-nitroanisole Chemical compound COC1=CC=CC=C1[N+]([O-])=O CFBYEGUGFPZCNF-UHFFFAOYSA-N 0.000 description 1
IQUPABOKLQSFBK-UHFFFAOYSA-N 2-nitrophenol Chemical compound OC1=CC=CC=C1[N+]([O-])=O IQUPABOKLQSFBK-UHFFFAOYSA-N 0.000 description 1
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical class COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
206010013710 Drug interaction Diseases 0.000 description 1
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-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
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
239000003513 alkali Substances 0.000 description 1
125000005907 alkyl ester group Chemical group 0.000 description 1
230000002862 amidating effect Effects 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
125000006360 carbonyl amino methylene group Chemical group [H]N(C([*:1])=O)C([H])([H])[*:2] 0.000 description 1
125000002843 carboxylic acid group Chemical group 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
MCWXGJITAZMZEV-UHFFFAOYSA-N dimethoate Chemical compound CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-UHFFFAOYSA-N 0.000 description 1
238000004821 distillation Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
230000032050 esterification Effects 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000012467 final product Substances 0.000 description 1
230000002140 halogenating effect Effects 0.000 description 1
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 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
150000002689 maleic acids Chemical class 0.000 description 1
239000000463 material Substances 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 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
150000002989 phenols Chemical class 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
235000014786 phosphorus Nutrition 0.000 description 1
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
231100000614 poison Toxicity 0.000 description 1
230000007096 poisonous effect Effects 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
VMPYTOIPVPQDNX-UHFFFAOYSA-N pyrrolidin-1-ylmethanamine Chemical compound NCN1CCCC1 VMPYTOIPVPQDNX-UHFFFAOYSA-N 0.000 description 1
230000036647 reaction Effects 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
229960004889 salicylic acid Drugs 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
150000003388 sodium compounds Chemical class 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 1
229940124530 sulfonamide Drugs 0.000 description 1
125000000565 sulfonamide group Chemical group 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
- C07C311/16—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/78—Halides of sulfonic acids
- C07C309/86—Halides of sulfonic acids having halosulfonyl groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C309/89—Halides of sulfonic acids having halosulfonyl groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing carboxyl groups bound to the carbon skeleton
- 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
- C07D207/04—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 no double bonds between ring members or between ring members and non-ring members
- C07D207/08—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 no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
- C07D207/09—Radicals substituted by nitrogen atoms, not forming part of a nitro radical

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Pyrrole Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Cosmetics (AREA)

CA248,976A 1975-03-28 1976-03-26 Process for preparing 1-ethyl-2-/2'-methoxy-5'-sulphonamidobenzoyl/-aminomethylpyrrolidine and its salts Expired CA1055951A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
HUGO1307A HU169703B (da)	1975-03-28	1975-03-28

Publications (1)

Publication Number	Publication Date
CA1055951A true CA1055951A (en)	1979-06-05

Family

ID=10996789

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA248,976A Expired CA1055951A (en)	1975-03-28	1976-03-26	Process for preparing 1-ethyl-2-/2'-methoxy-5'-sulphonamidobenzoyl/-aminomethylpyrrolidine and its salts

Country Status (17)

Country	Link
JP (1)	JPS51125380A (da)
AU (1)	AU501988B2 (da)
BG (1)	BG26522A3 (da)
CA (1)	CA1055951A (da)
CH (1)	CH619452A5 (da)
CS (1)	CS194754B2 (da)
DD (1)	DD124418A1 (da)
DE (1)	DE2613394A1 (da)
DK (1)	DK128176A (da)
ES (1)	ES446448A1 (da)
FI (1)	FI61878C (da)
GB (1)	GB1492166A (da)
HU (1)	HU169703B (da)
RO (1)	RO68720A (da)
SE (1)	SE410186B (da)
SU (1)	SU626693A3 (da)
YU (1)	YU79676A (da)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IT202200011363A1 (it) *	2022-05-30	2023-11-30	Univ Degli Studi Di Torino	Composti cristallini della sulpiride

1975
- 1975-03-28 HU HUGO1307A patent/HU169703B/hu unknown
1976
- 1976-03-23 DK DK128176A patent/DK128176A/da not_active Application Discontinuation
- 1976-03-24 AU AU12291/76A patent/AU501988B2/en not_active Expired
- 1976-03-25 CS CS761952A patent/CS194754B2/cs unknown
- 1976-03-25 DD DD192034A patent/DD124418A1/xx unknown
- 1976-03-26 SU SU762338456A patent/SU626693A3/ru active
- 1976-03-26 GB GB12264/76A patent/GB1492166A/en not_active Expired
- 1976-03-26 BG BG032715A patent/BG26522A3/xx unknown
- 1976-03-26 SE SE7603698A patent/SE410186B/xx not_active Application Discontinuation
- 1976-03-26 YU YU00796/76A patent/YU79676A/xx unknown
- 1976-03-26 JP JP51033458A patent/JPS51125380A/ja active Pending
- 1976-03-26 FI FI760827A patent/FI61878C/fi not_active IP Right Cessation
- 1976-03-26 CH CH380976A patent/CH619452A5/de not_active IP Right Cessation
- 1976-03-26 CA CA248,976A patent/CA1055951A/en not_active Expired
- 1976-03-27 ES ES446448A patent/ES446448A1/es not_active Expired
- 1976-03-27 RO RO7685333A patent/RO68720A/ro unknown
- 1976-03-29 DE DE19762613394 patent/DE2613394A1/de not_active Withdrawn

Also Published As

Publication number	Publication date
CS194754B2 (en)	1979-12-31
YU79676A (en)	1982-06-30
GB1492166A (en)	1977-11-16
FI760827A7 (da)	1976-09-29
ES446448A1 (es)	1977-06-16
HU169703B (da)	1977-02-28
CH619452A5 (en)	1980-09-30
DD124418A1 (da)	1977-02-23
AU501988B2 (en)	1979-07-12
FI61878C (fi)	1982-10-11
DE2613394A1 (de)	1976-10-07
BG26522A3 (bg)	1979-04-12
SE410186B (sv)	1979-10-01
FI61878B (fi)	1982-06-30
SE7603698L (sv)	1976-09-29
SU626693A3 (ru)	1978-09-30
JPS51125380A (en)	1976-11-01
DK128176A (da)	1976-09-29
RO68720A (ro)	1982-10-11
AU1229176A (en)	1977-09-29

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