CS240982B2 - Production method of pyrrolidine derivatives - Google Patents

Production method of pyrrolidine derivatives Download PDF

Info

Publication number: CS240982B2
Authority: CS; Czechoslovakia
Prior art keywords: total; formula; alkyl; pyrrolidinone; hydrogen
Prior art date: 1982-12-07

Application number

CS839041A

Other languages

Czech (cs)

English (en)

Other versions

CS904183A2 (en

Inventor

Jean L Fabre

Daniel Farge

Claude James

Daniel Lave

Original Assignee

Rhone Poulenc Sante

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.)

1982-12-07

Filing date

1983-12-02

Publication date

1986-03-13

1983-12-02 Application filed by Rhone Poulenc Sante filed Critical Rhone Poulenc Sante

1985-06-13 Publication of CS904183A2 publication Critical patent/CS904183A2/cs

1986-03-13 Publication of CS240982B2 publication Critical patent/CS240982B2/cs

Links

150000003235 pyrrolidines Chemical class 0.000 title claims 3
238000004519 manufacturing process Methods 0.000 title 1
150000001875 compounds Chemical class 0.000 claims description 23
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 17
150000003839 salts Chemical class 0.000 claims description 17
238000000034 method Methods 0.000 claims description 12
229910052739 hydrogen Inorganic materials 0.000 claims description 11
239000001257 hydrogen Substances 0.000 claims description 11
239000002253 acid Substances 0.000 claims description 10
125000000217 alkyl group Chemical group 0.000 claims description 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
229910052757 nitrogen Inorganic materials 0.000 claims description 6
HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 6
125000003545 alkoxy group Chemical group 0.000 claims description 5
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 5
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
150000007513 acids Chemical class 0.000 claims description 3
125000004432 carbon atom Chemical group C* 0.000 claims description 3
229910052736 halogen Inorganic materials 0.000 claims description 3
150000002367 halogens Chemical class 0.000 claims description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
229910052698 phosphorus Inorganic materials 0.000 claims description 3
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 3
125000004663 dialkyl amino group Chemical group 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 claims 1
125000004429 atom Chemical group 0.000 claims 1
125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 153
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 78
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 65
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 57
239000000203 mixture Substances 0.000 description 55
238000001914 filtration Methods 0.000 description 43
239000000243 solution Substances 0.000 description 43
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OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
239000000706 filtrate Substances 0.000 description 18
ZXRWQRYMEYRQKX-UHFFFAOYSA-N 5-ethoxypyrrolidin-2-one Chemical compound CCOC1CCC(=O)N1 ZXRWQRYMEYRQKX-UHFFFAOYSA-N 0.000 description 17
238000001816 cooling Methods 0.000 description 17
239000012043 crude product Substances 0.000 description 13
-1 non-toxic salts Chemical class 0.000 description 13
238000003756 stirring Methods 0.000 description 13
238000004821 distillation Methods 0.000 description 12
238000002844 melting Methods 0.000 description 11
230000008018 melting Effects 0.000 description 11
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 10
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
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OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 8
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 8
229910052700 potassium Inorganic materials 0.000 description 8
239000011591 potassium Substances 0.000 description 8
MKJIEFSOBYUXJB-HOCLYGCPSA-N (3S,11bS)-9,10-dimethoxy-3-isobutyl-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-one Chemical compound C1CN2C[C@H](CC(C)C)C(=O)C[C@H]2C2=C1C=C(OC)C(OC)=C2 MKJIEFSOBYUXJB-HOCLYGCPSA-N 0.000 description 7
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239000000126 substance Substances 0.000 description 4
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
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ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
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150000002148 esters Chemical class 0.000 description 3
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TXFPEBPIARQUIG-UHFFFAOYSA-N 4'-hydroxyacetophenone Chemical compound CC(=O)C1=CC=C(O)C=C1 TXFPEBPIARQUIG-UHFFFAOYSA-N 0.000 description 2
YJNXXQSTMMENPY-UHFFFAOYSA-N 5-[4-(4-methoxyphenyl)piperazin-1-yl]pyrrolidin-2-one Chemical compound C1=CC(OC)=CC=C1N1CCN(C2NC(=O)CC2)CC1 YJNXXQSTMMENPY-UHFFFAOYSA-N 0.000 description 2
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
241000699670 Mus sp. Species 0.000 description 2
229920002472 Starch Polymers 0.000 description 2
UCTLHLZWKJIXJI-LXIBVNSESA-N [(3s,8r,9s,10r,13s,14s)-17-chloro-16-formyl-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15-decahydro-1h-cyclopenta[a]phenanthren-3-yl] acetate Chemical compound C([C@@H]12)C[C@]3(C)C(Cl)=C(C=O)C[C@H]3[C@@H]1CC=C1[C@]2(C)CC[C@H](OC(=O)C)C1 UCTLHLZWKJIXJI-LXIBVNSESA-N 0.000 description 2
239000004480 active ingredient Substances 0.000 description 2
230000001430 anti-depressive effect Effects 0.000 description 2
239000000935 antidepressant agent Substances 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
238000009833 condensation Methods 0.000 description 2
230000005494 condensation Effects 0.000 description 2
239000003085 diluting agent Substances 0.000 description 2
230000000694 effects Effects 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
239000000284 extract Substances 0.000 description 2
238000009472 formulation Methods 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
239000003701 inert diluent Substances 0.000 description 2
239000007788 liquid Substances 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
125000006501 nitrophenyl group Chemical group 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
YZTJYBJCZXZGCT-UHFFFAOYSA-N phenylpiperazine Chemical compound C1CNCCN1C1=CC=CC=C1 YZTJYBJCZXZGCT-UHFFFAOYSA-N 0.000 description 2
229920001223 polyethylene glycol Polymers 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
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239000003381 stabilizer Substances 0.000 description 2
239000008107 starch Substances 0.000 description 2
235000019698 starch Nutrition 0.000 description 2
238000007920 subcutaneous administration Methods 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 2
239000000725 suspension Substances 0.000 description 2
231100000419 toxicity Toxicity 0.000 description 2
230000001988 toxicity Effects 0.000 description 2
235000015112 vegetable and seed oil Nutrition 0.000 description 2
239000008158 vegetable oil Substances 0.000 description 2
PWZDJIUQHUGFRJ-UHFFFAOYSA-N 1-(2-chlorophenyl)piperazine Chemical compound ClC1=CC=CC=C1N1CCNCC1 PWZDJIUQHUGFRJ-UHFFFAOYSA-N 0.000 description 1
QSTMOHFZTDLSBZ-UHFFFAOYSA-N 1-(3,4,5-trimethoxyphenyl)piperazine Chemical compound COC1=C(OC)C(OC)=CC(N2CCNCC2)=C1 QSTMOHFZTDLSBZ-UHFFFAOYSA-N 0.000 description 1
VHFVKMTVMIZMIK-UHFFFAOYSA-N 1-(3-chlorophenyl)piperazine Chemical compound ClC1=CC=CC(N2CCNCC2)=C1 VHFVKMTVMIZMIK-UHFFFAOYSA-N 0.000 description 1
JIWHIRLNKIUYSM-UHFFFAOYSA-N 1-(3-methylphenyl)piperazine Chemical compound CC1=CC=CC(N2CCNCC2)=C1 JIWHIRLNKIUYSM-UHFFFAOYSA-N 0.000 description 1
AVJKDKWRVSSJPK-UHFFFAOYSA-N 1-(4-fluorophenyl)piperazine Chemical compound C1=CC(F)=CC=C1N1CCNCC1 AVJKDKWRVSSJPK-UHFFFAOYSA-N 0.000 description 1
ONEYFZXGNFNRJH-UHFFFAOYSA-N 1-(4-methylphenyl)piperazine Chemical compound C1=CC(C)=CC=C1N1CCNCC1 ONEYFZXGNFNRJH-UHFFFAOYSA-N 0.000 description 1
VWOJSRICSKDKAW-UHFFFAOYSA-N 1-(4-nitrophenyl)piperazine Chemical compound C1=CC([N+](=O)[O-])=CC=C1N1CCNCC1 VWOJSRICSKDKAW-UHFFFAOYSA-N 0.000 description 1
KPXVKKBJROCIJB-UHFFFAOYSA-N 1-(4-piperazin-1-ylphenyl)ethanone Chemical compound C1=CC(C(=O)C)=CC=C1N1CCNCC1 KPXVKKBJROCIJB-UHFFFAOYSA-N 0.000 description 1
SOVLQDJRXJFKHO-UHFFFAOYSA-N 1-[4-chloro-3-(trifluoromethyl)phenyl]piperazine Chemical compound C1=C(Cl)C(C(F)(F)F)=CC(N2CCNCC2)=C1 SOVLQDJRXJFKHO-UHFFFAOYSA-N 0.000 description 1
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AKUNSTOMHUXJOZ-UHFFFAOYSA-N 1-hydroperoxybutane Chemical compound CCCCOO AKUNSTOMHUXJOZ-UHFFFAOYSA-N 0.000 description 1
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125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
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125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 description 1
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KBKLRUPXGOHQJC-UHFFFAOYSA-N 5-[4-(3-methylphenyl)piperazin-1-yl]pyrrolidin-2-one Chemical compound CC1=CC=CC(N2CCN(CC2)C2NC(=O)CC2)=C1 KBKLRUPXGOHQJC-UHFFFAOYSA-N 0.000 description 1
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229940093471 ethyl oleate Drugs 0.000 description 1
238000000605 extraction Methods 0.000 description 1
210000000744 eyelid Anatomy 0.000 description 1
206010016256 fatigue Diseases 0.000 description 1
239000012467 final product Substances 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
235000013355 food flavoring agent Nutrition 0.000 description 1
235000003599 food sweetener Nutrition 0.000 description 1
VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
239000011521 glass Substances 0.000 description 1
125000005456 glyceride group Chemical group 0.000 description 1
239000008187 granular material Substances 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
238000010348 incorporation Methods 0.000 description 1
239000002198 insoluble material Substances 0.000 description 1
238000002955 isolation Methods 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000004922 lacquer Substances 0.000 description 1
239000008101 lactose Substances 0.000 description 1
231100000636 lethal dose Toxicity 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
150000002688 maleic acid derivatives Chemical class 0.000 description 1
239000002609 medium Substances 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-M methanesulfonate group Chemical class CS(=O)(=O)[O-] AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
238000002156 mixing Methods 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
GRJIAPLFQXLDJJ-UHFFFAOYSA-N n,n-dimethyl-4-piperazin-1-ylaniline Chemical compound C1=CC(N(C)C)=CC=C1N1CCNCC1 GRJIAPLFQXLDJJ-UHFFFAOYSA-N 0.000 description 1
AYOOGWWGECJQPI-NSHDSACASA-N n-[(1s)-1-(5-fluoropyrimidin-2-yl)ethyl]-3-(3-propan-2-yloxy-1h-pyrazol-5-yl)imidazo[4,5-b]pyridin-5-amine Chemical compound N1C(OC(C)C)=CC(N2C3=NC(N[C@@H](C)C=4N=CC(F)=CN=4)=CC=C3N=C2)=N1 AYOOGWWGECJQPI-NSHDSACASA-N 0.000 description 1
150000002823 nitrates Chemical class 0.000 description 1
239000012457 nonaqueous media Substances 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
239000003921 oil Substances 0.000 description 1
235000019198 oils Nutrition 0.000 description 1
235000008390 olive oil Nutrition 0.000 description 1
239000004006 olive oil Substances 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000002895 organic esters Chemical class 0.000 description 1
UNEIHNMKASENIG-UHFFFAOYSA-N para-chlorophenylpiperazine Chemical compound C1=CC(Cl)=CC=C1N1CCNCC1 UNEIHNMKASENIG-UHFFFAOYSA-N 0.000 description 1
MRDGZSKYFPGAKP-UHFFFAOYSA-N para-methoxyphenylpiperazine Chemical compound C1=CC(OC)=CC=C1N1CCNCC1 MRDGZSKYFPGAKP-UHFFFAOYSA-N 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
239000006187 pill Substances 0.000 description 1
RFIOZSIHFNEKFF-UHFFFAOYSA-N piperazine-1-carboxylic acid Chemical class OC(=O)N1CCNCC1 RFIOZSIHFNEKFF-UHFFFAOYSA-N 0.000 description 1
125000004193 piperazinyl group Chemical group 0.000 description 1
239000004014 plasticizer Substances 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
239000000843 powder Substances 0.000 description 1
210000002307 prostate Anatomy 0.000 description 1
208000018299 prostration Diseases 0.000 description 1
201000003004 ptosis Diseases 0.000 description 1
238000000746 purification Methods 0.000 description 1
QFYXSLAAXZTRLG-UHFFFAOYSA-N pyrrolidine-2,3-dione Chemical compound O=C1CCNC1=O QFYXSLAAXZTRLG-UHFFFAOYSA-N 0.000 description 1
230000005855 radiation Effects 0.000 description 1
150000003873 salicylate salts Chemical class 0.000 description 1
230000036280 sedation Effects 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
230000003381 solubilizing effect Effects 0.000 description 1
230000001954 sterilising effect Effects 0.000 description 1
238000004659 sterilization and disinfection Methods 0.000 description 1
239000003206 sterilizing agent Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
150000003890 succinate salts Chemical class 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
229960000278 theophylline Drugs 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
235000012431 wafers Nutrition 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
- C07D207/18—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 one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—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 one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/273—2-Pyrrolidones with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to other ring carbon atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- 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
- C07D207/18—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 one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—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 one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
- 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
- C07D295/04—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/135—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Neurosurgery (AREA)
Biomedical Technology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Life Sciences & Earth Sciences (AREA)
Neurology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Pyrrole Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Plural Heterocyclic Compounds (AREA)
Steroid Compounds (AREA)
Luminescent Compositions (AREA)

CS839041A 1982-12-07 1983-12-02 Production method of pyrrolidine derivatives CS240982B2 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
FR8220492A FR2537133A1 (fr)	1982-12-07	1982-12-07	Nouveaux derives de la (piperazinyl-1)-5 pyrrolidine, leur preparation et les medicaments qui les contiennent

Publications (2)

Publication Number	Publication Date
CS904183A2 CS904183A2 (en)	1985-06-13
CS240982B2 true CS240982B2 (en)	1986-03-13

Family

ID=9279863

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS839041A CS240982B2 (en)	1982-12-07	1983-12-02	Production method of pyrrolidine derivatives

Country Status (25)

Country	Link
US (1)	US4547504A (de)
EP (1)	EP0110795B1 (de)
JP (1)	JPS59110670A (de)
AT (1)	ATE18548T1 (de)
AU (1)	AU560075B2 (de)
BG (1)	BG40808A3 (de)
CA (1)	CA1208645A (de)
CS (1)	CS240982B2 (de)
DD (1)	DD213216A5 (de)
DE (1)	DE3362566D1 (de)
DK (1)	DK562783A (de)
ES (1)	ES527897A0 (de)
FI (1)	FI76320C (de)
FR (1)	FR2537133A1 (de)
GR (1)	GR72855B (de)
HU (1)	HU191903B (de)
IE (1)	IE56453B1 (de)
IL (1)	IL70396A (de)
MA (1)	MA19966A1 (de)
NO (1)	NO158218C (de)
NZ (1)	NZ206498A (de)
PL (1)	PL141385B1 (de)
PT (1)	PT77774B (de)
SU (1)	SU1240359A3 (de)
ZA (1)	ZA839070B (de)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0241053B1 (de) *	1986-02-27	1992-11-11	Duphar International Research B.V	Aryl-substituierte(N-piperidinyl)methyl und (N-piperazinyl)methylazole mit antipsychotischer Wirkung
DK0402644T3 (da) *	1989-05-19	1996-01-02	Hoechst Roussel Pharma	N-(Aryloxyalkyl)-heteroarylpiperidiner og -heteroarylpiperaziner, fremgangsmåde til deres fremstilli ng samt deres anvendelse som medikamenter
US5066663A (en) *	1990-05-21	1991-11-19	Warner-Lambert Company	Substituted-hetero-cyclopentanones and cyclopentenones and derivatives thereof acting at muscarinic receptors
DE19540027A1 (de) *	1995-10-27	1997-04-30	Gruenenthal Gmbh	Substituierte Imidazolidin-2,4-dion-Verbindungen als pharmazeutische Wirkstoffe
US6897213B1 (en)	1995-11-21	2005-05-24	Warner-Lambert Company	Heterocycles as cholecystokinin (CCK) ligands
US5969138A (en) *	1996-11-01	1999-10-19	Mitsui Chemicals, Inc.	Pyrrolidinone derivatives
BR9814820A (pt) *	1997-10-14	2000-10-03	Welfide Corp	Compostos de piperazina e seu uso médico

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4247549A (en) *	1978-12-27	1981-01-27	Ici Americas Inc.	Piperazine-1-carboxylic acid esters possessing antidepressant or analgesic activity

1982
- 1982-12-07 FR FR8220492A patent/FR2537133A1/fr active Granted
1983
- 1983-12-02 CS CS839041A patent/CS240982B2/cs unknown
- 1983-12-05 GR GR73154A patent/GR72855B/el unknown
- 1983-12-05 DD DD83257518A patent/DD213216A5/de unknown
- 1983-12-05 FI FI834453A patent/FI76320C/fi not_active IP Right Cessation
- 1983-12-05 PL PL1983244921A patent/PL141385B1/pl unknown
- 1983-12-06 NZ NZ206498A patent/NZ206498A/en unknown
- 1983-12-06 CA CA000442681A patent/CA1208645A/fr not_active Expired
- 1983-12-06 US US06/558,775 patent/US4547504A/en not_active Expired - Fee Related
- 1983-12-06 IL IL70396A patent/IL70396A/xx not_active IP Right Cessation
- 1983-12-06 DK DK562783A patent/DK562783A/da not_active Application Discontinuation
- 1983-12-06 MA MA20187A patent/MA19966A1/fr unknown
- 1983-12-06 JP JP58229251A patent/JPS59110670A/ja active Pending
- 1983-12-06 DE DE8383402354T patent/DE3362566D1/de not_active Expired
- 1983-12-06 ZA ZA839070A patent/ZA839070B/xx unknown
- 1983-12-06 PT PT77774A patent/PT77774B/pt unknown
- 1983-12-06 HU HU834166A patent/HU191903B/hu unknown
- 1983-12-06 AT AT83402354T patent/ATE18548T1/de not_active IP Right Cessation
- 1983-12-06 IE IE2867/83A patent/IE56453B1/xx unknown
- 1983-12-06 EP EP83402354A patent/EP0110795B1/de not_active Expired
- 1983-12-06 AU AU22108/83A patent/AU560075B2/en not_active Ceased
- 1983-12-06 SU SU833673511A patent/SU1240359A3/ru active
- 1983-12-06 NO NO834481A patent/NO158218C/no unknown
- 1983-12-07 BG BG063371A patent/BG40808A3/xx unknown
- 1983-12-07 ES ES527897A patent/ES527897A0/es active Granted

Also Published As

Publication number	Publication date
FR2537133B1 (de)	1985-05-17
DK562783D0 (da)	1983-12-06
ATE18548T1 (de)	1986-03-15
NO834481L (no)	1984-06-08
ES8406436A1 (es)	1984-08-01
IL70396A0 (en)	1984-03-30
NZ206498A (en)	1986-05-09
EP0110795B1 (de)	1986-03-12
JPS59110670A (ja)	1984-06-26
PL244921A1 (en)	1985-03-26
CS904183A2 (en)	1985-06-13
AU560075B2 (en)	1987-03-26
FI834453A0 (fi)	1983-12-05
EP0110795A1 (de)	1984-06-13
DD213216A5 (de)	1984-09-05
FI76320C (fi)	1988-10-10
ZA839070B (en)	1984-07-25
GR72855B (de)	1983-12-08
FI834453L (fi)	1984-06-08
CA1208645A (fr)	1986-07-29
AU2210883A (en)	1984-06-14
IE832867L (en)	1984-06-07
NO158218C (no)	1988-08-03
HU191903B (en)	1987-04-28
SU1240359A3 (ru)	1986-06-23
PT77774B (fr)	1986-07-11
ES527897A0 (es)	1984-08-01
IL70396A (en)	1986-11-30
PL141385B1 (en)	1987-07-31
PT77774A (fr)	1984-01-01
DE3362566D1 (en)	1986-04-17
US4547504A (en)	1985-10-15
BG40808A3 (bg)	1987-02-16
NO158218B (no)	1988-04-25
DK562783A (da)	1984-06-08
IE56453B1 (en)	1991-08-14
FR2537133A1 (fr)	1984-06-08
MA19966A1 (fr)	1984-07-01
FI76320B (fi)	1988-06-30

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US5919789A (en)	1999-07-06	Xanthines and their therapeutic use
EP0258755B1 (de)	1991-09-11	Alpha-alkyl-4-amino-3-chinolin-methanole und 1-(4-Aralkylamino-3-chinolyl)alkanone, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel
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US4670434A (en)	1987-06-02	(2-oxo-3-methylene-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolinyl)oxyalkylamides useful as cyclic AMP phosphodiesterase inhibitors
EP0198456B1 (de)	1992-06-10	1,7-Naphthyridinderivate und diese enthaltende Arzneimittel
DE60307875T2 (de)	2007-04-12	Imidazopyrin-derivate, verfahren zu ihrer herstellung und sie enthaltende pharmazeutische zusamensetzungen
KR870001483B1 (ko)	1987-08-13	코우마린 유도체와 그 염의 제조방법
US4960773A (en)	1990-10-02	Xanthine derivatives
EP0089028B1 (de)	1988-05-25	Neue Theophyllin-Derivate und Verfahren zu ihrer Herstellung
CA1256105A (en)	1989-06-20	Substituted 1,8-naphthyridinones, processes for their preparation and pharmaceutical compositions containing them
US3983239A (en)	1976-09-28	Hexahydro-γ-carboline derivatives and their salts
CS240982B2 (en)	1986-03-13	Production method of pyrrolidine derivatives
EP0383171A2 (de)	1990-08-22	2,3,23-Trihydroxy-urs-12-en Derivate zur Behandlung von Kognitiven Störungen
US3888983A (en)	1975-06-10	Derivatives of thiazolino-pyrimidin-6-ones, in inducing analgesia
US4049816A (en)	1977-09-20	Antiviral 2-amino-5-[1-(indol-3-yl)alkyl]-2-thiazolin-4-ones
EP0575425A1 (de)	1993-12-29	VERWENDUNG VON OXAZOLO- 2,3-a]ISOINDOL- UND IMIDAZO 2,1-a]ISOINDOL-DERIVATEN ALS ANTIVIRALE ARZNEIMITTEL SOWIE NEUE OXAZOLO 2,3-a]ISOINDOL-DERIVATEN.
KR900006745B1 (ko)	1990-09-20	5-아미노-1,2-디티올-3-온 화합물 및 그의 제법
EP0039919B1 (de)	1983-12-28	Benzoxazol und Benzothiazol-Derivate mit antiallergischer Wirkung
DE3432985C2 (de)	1993-09-16
US3523120A (en)	1970-08-04	Piperonyl-piperazine compounds
SU1447283A3 (ru)	1988-12-23	Способ получени конденсированных производных @ S-триазина
EP0079639A1 (de)	1983-05-25	Entzündunghemmendes Heilmittel
IL37431A (en)	1974-10-22	Pharmaceutical compositions containing derivatives of thiazolino(3,2-a)pyrimidin-5-one,certain such novel derivatives and their preparation
US3989689A (en)	1976-11-02	4-Carbamoyl-1-benzazepines
SU1072809A3 (ru)	1984-02-07	Способ получени тиадиазолтетрагидроизохинолина или его фармацевтически приемлемой кислотно-аддитивной соли