CA1039731A - Synthese de derives de methoxy-2 benzamide - Google Patents

Synthese de derives de methoxy-2 benzamide

Info

Publication number: CA1039731A
Authority: CA; Canada
Prior art keywords: formula; alkyl; process according; carbon atoms; methyl
Prior art date: 1974-12-18
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

CA241,723A

Other languages

English (en)

Other versions

CA241723S (en

Inventor

Henry Najer

Don P.R.L. Giudicelli

Maurice Jalfre

Daniel C.L. Obitz

Philippe M.J. Manoury

Jean-Pierre Kaplan

Bernard M. Raizon

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.)

Synthelabo SA

Original Assignee

Synthelabo SA

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.)

1974-12-18

Filing date

1975-12-15

Publication date

1978-10-03

1974-12-18 Priority claimed from FR7441718A external-priority patent/FR2294698A1/fr

1975-10-14 Priority claimed from FR7531334A external-priority patent/FR2327771A2/fr

1975-11-13 Priority claimed from FR7534570A external-priority patent/FR2331345A2/fr

1975-12-15 Application filed by Synthelabo SA filed Critical Synthelabo SA

1978-10-03 Application granted granted Critical

1978-10-03 Publication of CA1039731A publication Critical patent/CA1039731A/fr

Status Expired legal-status Critical Current

Links

MNWSGMTUGXNYHJ-UHFFFAOYSA-N 2-methoxybenzamide Chemical class COC1=CC=CC=C1C(N)=O MNWSGMTUGXNYHJ-UHFFFAOYSA-N 0.000 title claims abstract description 7
238000004519 manufacturing process Methods 0.000 title 1
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 32
150000003839 salts Chemical class 0.000 claims abstract description 32
125000000217 alkyl group Chemical group 0.000 claims abstract description 31
239000000460 chlorine Substances 0.000 claims abstract description 29
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 24
239000002253 acid Substances 0.000 claims abstract description 20
239000001257 hydrogen Substances 0.000 claims abstract description 16
229910052801 chlorine Inorganic materials 0.000 claims abstract description 14
229910052736 halogen Inorganic materials 0.000 claims abstract description 13
150000002367 halogens Chemical group 0.000 claims abstract description 13
125000003545 alkoxy group Chemical group 0.000 claims abstract description 10
230000003287 optical effect Effects 0.000 claims abstract description 10
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 10
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 8
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 7
125000002947 alkylene group Chemical group 0.000 claims abstract description 5
150000001875 compounds Chemical class 0.000 claims description 66
238000000034 method Methods 0.000 claims description 54
-1 cycloalkyl-alkyl radical Chemical group 0.000 claims description 37
239000000126 substance Substances 0.000 claims description 19
RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 13
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
150000001412 amines Chemical class 0.000 claims description 9
238000002360 preparation method Methods 0.000 claims description 7
125000000565 sulfonamide group Chemical group 0.000 claims description 7
239000007858 starting material Substances 0.000 claims description 5
ILUJQPXNXACGAN-UHFFFAOYSA-N O-methylsalicylic acid Chemical compound COC1=CC=CC=C1C(O)=O ILUJQPXNXACGAN-UHFFFAOYSA-N 0.000 claims description 4
125000004429 atom Chemical group 0.000 claims description 4
238000006243 chemical reaction Methods 0.000 claims description 4
125000004175 fluorobenzyl group Chemical group 0.000 claims description 4
150000003141 primary amines Chemical class 0.000 claims description 4
125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 3
125000004803 chlorobenzyl group Chemical group 0.000 claims description 3
125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 claims description 3
125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 3
ZPSJGADGUYYRKE-UHFFFAOYSA-N 2H-pyran-2-one Chemical compound O=C1C=CC=CO1 ZPSJGADGUYYRKE-UHFFFAOYSA-N 0.000 claims description 2
RHDGNLCLDBVESU-UHFFFAOYSA-N but-3-en-4-olide Chemical compound O=C1CC=CO1 RHDGNLCLDBVESU-UHFFFAOYSA-N 0.000 claims description 2
150000004820 halides Chemical class 0.000 claims description 2
150000003235 pyrrolidines Chemical class 0.000 claims description 2
150000003335 secondary amines Chemical class 0.000 claims description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 9
125000001309 chloro group Chemical group Cl* 0.000 claims 7
229910006074 SO2NH2 Inorganic materials 0.000 claims 5
125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 5
125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims 3
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical class C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 2
125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 claims 2
125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 2
125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims 2
XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 claims 2
125000006493 trifluoromethyl benzyl group Chemical group 0.000 claims 2
SKKTZJVNTSSCLS-UHFFFAOYSA-N 2-(nitromethylidene)piperidine Chemical compound [O-][N+](=O)C=C1CCCCN1 SKKTZJVNTSSCLS-UHFFFAOYSA-N 0.000 claims 1
MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical class C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 claims 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
230000002152 alkylating effect Effects 0.000 claims 1
125000000950 dibromo group Chemical group Br* 0.000 claims 1
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract description 2
208000028017 Psychotic disease Diseases 0.000 abstract description 2
229910052731 fluorine Inorganic materials 0.000 abstract description 2
239000011737 fluorine Substances 0.000 abstract description 2
150000002431 hydrogen Chemical group 0.000 abstract 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 38
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 38
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 36
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 32
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 28
239000000203 mixture Substances 0.000 description 27
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
238000002844 melting Methods 0.000 description 15
230000008018 melting Effects 0.000 description 15
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 14
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
239000002585 base Substances 0.000 description 12
238000003756 stirring Methods 0.000 description 11
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
238000010992 reflux Methods 0.000 description 10
239000000155 melt Substances 0.000 description 9
239000002904 solvent Substances 0.000 description 9
238000004458 analytical method Methods 0.000 description 8
238000009835 boiling Methods 0.000 description 8
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 8
229910052753 mercury Inorganic materials 0.000 description 8
239000000047 product Substances 0.000 description 8
241000699670 Mus sp. Species 0.000 description 7
230000000694 effects Effects 0.000 description 7
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 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
AFVFQIVMOAPDHO-UHFFFAOYSA-M Methanesulfonate Chemical compound CS([O-])(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 6
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
239000013078 crystal Substances 0.000 description 6
238000007912 intraperitoneal administration Methods 0.000 description 6
229910052943 magnesium sulfate Inorganic materials 0.000 description 6
235000019341 magnesium sulphate Nutrition 0.000 description 6
239000007787 solid Substances 0.000 description 6
KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 5
231100000111 LD50 Toxicity 0.000 description 5
239000003610 charcoal Substances 0.000 description 5
239000000706 filtrate Substances 0.000 description 5
229910000027 potassium carbonate Inorganic materials 0.000 description 5
230000000506 psychotropic effect Effects 0.000 description 5
229960004940 sulpiride Drugs 0.000 description 5
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
241000700159 Rattus Species 0.000 description 4
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
VMWNQDUVQKEIOC-CYBMUJFWSA-N apomorphine Chemical compound C([C@H]1N(C)CC2)C3=CC=C(O)C(O)=C3C3=C1C2=CC=C3 VMWNQDUVQKEIOC-CYBMUJFWSA-N 0.000 description 4
229960004046 apomorphine Drugs 0.000 description 4
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 4
238000010438 heat treatment Methods 0.000 description 4
230000007935 neutral effect Effects 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
239000000725 suspension Substances 0.000 description 4
YONLFQNRGZXBBF-ZIAGYGMSSA-N (2r,3r)-2,3-dibenzoyloxybutanedioic acid Chemical compound O([C@@H](C(=O)O)[C@@H](OC(=O)C=1C=CC=CC=1)C(O)=O)C(=O)C1=CC=CC=C1 YONLFQNRGZXBBF-ZIAGYGMSSA-N 0.000 description 3
208000009132 Catalepsy Diseases 0.000 description 3
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
206010047853 Waxy flexibility Diseases 0.000 description 3
BOKXGTOMUFSZQX-UHFFFAOYSA-N [1-[(4-fluorophenyl)methyl]pyrrolidin-2-yl]methanamine Chemical compound NCC1CCCN1CC1=CC=C(F)C=C1 BOKXGTOMUFSZQX-UHFFFAOYSA-N 0.000 description 3
230000007059 acute toxicity Effects 0.000 description 3
231100000403 acute toxicity Toxicity 0.000 description 3
150000001408 amides Chemical class 0.000 description 3
230000003474 anti-emetic effect Effects 0.000 description 3
ZHNUHDYFZUAESO-UHFFFAOYSA-N formamide Substances NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 3
238000001990 intravenous administration Methods 0.000 description 3
239000007788 liquid Substances 0.000 description 3
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
239000000377 silicon dioxide Substances 0.000 description 3
YONLFQNRGZXBBF-KBPBESRZSA-N (2s,3s)-2,3-dibenzoyloxybutanedioic acid Chemical compound O([C@H](C(=O)O)[C@H](OC(=O)C=1C=CC=CC=1)C(O)=O)C(=O)C1=CC=CC=C1 YONLFQNRGZXBBF-KBPBESRZSA-N 0.000 description 2
IIFVWLUQBAIPMJ-UHFFFAOYSA-N (4-fluorophenyl)methanamine Chemical compound NCC1=CC=C(F)C=C1 IIFVWLUQBAIPMJ-UHFFFAOYSA-N 0.000 description 2
KZKRGOSWLGSOEZ-UHFFFAOYSA-N 1-[(4-fluorophenyl)methyl]pyrrolidin-2-one Chemical compound C1=CC(F)=CC=C1CN1C(=O)CCC1 KZKRGOSWLGSOEZ-UHFFFAOYSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
241000282472 Canis lupus familiaris Species 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
206010012219 Deliria Diseases 0.000 description 2
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
208000019695 Migraine disease Diseases 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
239000007868 Raney catalyst Substances 0.000 description 2
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
229910000564 Raney nickel Inorganic materials 0.000 description 2
206010042008 Stereotypy Diseases 0.000 description 2
208000012886 Vertigo Diseases 0.000 description 2
ZBIQUHZPSAZOIM-UHFFFAOYSA-N [1-[(4-chlorophenyl)methyl]pyrrolidin-2-yl]methanamine Chemical compound NCC1CCCN1CC1=CC=C(Cl)C=C1 ZBIQUHZPSAZOIM-UHFFFAOYSA-N 0.000 description 2
239000004411 aluminium Substances 0.000 description 2
229910052782 aluminium Inorganic materials 0.000 description 2
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
230000008485 antagonism Effects 0.000 description 2
230000003354 anti-apomorphinic effect Effects 0.000 description 2
230000003542 behavioural effect Effects 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
230000003001 depressive effect Effects 0.000 description 2
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
JROGBPMEKVAPEH-GXGBFOEMSA-N emetine dihydrochloride Chemical compound Cl.Cl.N1CCC2=CC(OC)=C(OC)C=C2[C@H]1C[C@H]1C[C@H]2C3=CC(OC)=C(OC)C=C3CCN2C[C@@H]1CC JROGBPMEKVAPEH-GXGBFOEMSA-N 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
239000000284 extract Substances 0.000 description 2
YEJRWHAVMIAJKC-UHFFFAOYSA-N gamma-butyrolactone Natural products O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
239000011521 glass Substances 0.000 description 2
150000004678 hydrides Chemical class 0.000 description 2
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
229910000041 hydrogen chloride Inorganic materials 0.000 description 2
230000001939 inductive effect Effects 0.000 description 2
238000002955 isolation Methods 0.000 description 2
239000010410 layer Substances 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
206010027599 migraine Diseases 0.000 description 2
230000001962 neuropharmacologic effect Effects 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
238000007911 parenteral administration Methods 0.000 description 2
239000003208 petroleum Substances 0.000 description 2
239000000843 powder Substances 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
230000009758 senescence Effects 0.000 description 2
229940095064 tartrate Drugs 0.000 description 2
230000001225 therapeutic effect Effects 0.000 description 2
231100000419 toxicity Toxicity 0.000 description 2
230000001988 toxicity Effects 0.000 description 2
238000001665 trituration Methods 0.000 description 2
231100000889 vertigo Toxicity 0.000 description 2
DKWRQRNCULDABS-UHFFFAOYSA-N (1-benzylpiperidin-2-yl)methanamine Chemical compound NCC1CCCCN1CC1=CC=CC=C1 DKWRQRNCULDABS-UHFFFAOYSA-N 0.000 description 1
XBDXMDVEZLOGMC-UHFFFAOYSA-N 1-(chloromethyl)-3-fluorobenzene Chemical compound FC1=CC=CC(CCl)=C1 XBDXMDVEZLOGMC-UHFFFAOYSA-N 0.000 description 1
PFILPPRZPRFMFE-UHFFFAOYSA-N 1-[(4-chlorophenyl)methyl]-2-(nitromethylidene)pyrrolidine Chemical compound [O-][N+](=O)C=C1CCCN1CC1=CC=C(Cl)C=C1 PFILPPRZPRFMFE-UHFFFAOYSA-N 0.000 description 1
KRASCFFPLDBTOV-UHFFFAOYSA-N 1-[(4-fluorophenyl)methyl]-2-(nitromethylidene)pyrrolidine Chemical compound [O-][N+](=O)C=C1CCCN1CC1=CC=C(F)C=C1 KRASCFFPLDBTOV-UHFFFAOYSA-N 0.000 description 1
LKMGDZMCCPSUFI-UHFFFAOYSA-N 2-(nitromethylidene)pyrrolidine Chemical compound [O-][N+](=O)C=C1CCCN1 LKMGDZMCCPSUFI-UHFFFAOYSA-N 0.000 description 1
UUNIOFWUJYBVGQ-UHFFFAOYSA-N 2-amino-4-(3,4-dimethoxyphenyl)-10-fluoro-4,5,6,7-tetrahydrobenzo[1,2]cyclohepta[6,7-d]pyran-3-carbonitrile Chemical compound C1=C(OC)C(OC)=CC=C1C1C(C#N)=C(N)OC2=C1CCCC1=CC=C(F)C=C12 UUNIOFWUJYBVGQ-UHFFFAOYSA-N 0.000 description 1
GTKYLVJCMKDNTH-UHFFFAOYSA-N 2-methoxy-5-sulfamoylbenzamide Chemical compound COC1=CC=C(S(N)(=O)=O)C=C1C(N)=O GTKYLVJCMKDNTH-UHFFFAOYSA-N 0.000 description 1
XFZMCFJADJFEBB-UHFFFAOYSA-N 2-methoxy-5-sulfamoylbenzoyl chloride Chemical compound COC1=CC=C(S(N)(=O)=O)C=C1C(Cl)=O XFZMCFJADJFEBB-UHFFFAOYSA-N 0.000 description 1
AJVBPNRMKNARPG-UHFFFAOYSA-N 3-sulfamoylbenzamide Chemical compound NC(=O)C1=CC=CC(S(N)(=O)=O)=C1 AJVBPNRMKNARPG-UHFFFAOYSA-N 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
JVLUMHRASWENRU-UHFFFAOYSA-N 5-chloro-2-methoxybenzoyl chloride Chemical compound COC1=CC=C(Cl)C=C1C(Cl)=O JVLUMHRASWENRU-UHFFFAOYSA-N 0.000 description 1
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
208000019901 Anxiety disease Diseases 0.000 description 1
241000861718 Chloris <Aves> Species 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
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
239000001828 Gelatine Substances 0.000 description 1
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 1
206010022998 Irritability Diseases 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
208000008469 Peptic Ulcer Diseases 0.000 description 1
208000012545 Psychophysiologic disease Diseases 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
230000001154 acute effect Effects 0.000 description 1
230000001270 agonistic effect Effects 0.000 description 1
229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
150000008041 alkali metal carbonates Chemical class 0.000 description 1
WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
229910021502 aluminium hydroxide Inorganic materials 0.000 description 1
239000002111 antiemetic agent Substances 0.000 description 1
229940125683 antiemetic agent Drugs 0.000 description 1
230000036506 anxiety Effects 0.000 description 1
229940054066 benzamide antipsychotics Drugs 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000002775 capsule Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
230000009194 climbing Effects 0.000 description 1
229940125890 compound Ia Drugs 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
SDIXRDNYIMOKSG-UHFFFAOYSA-L disodium methyl arsenate Chemical compound [Na+].[Na+].C[As]([O-])([O-])=O SDIXRDNYIMOKSG-UHFFFAOYSA-L 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000008298 dragée Substances 0.000 description 1
239000003814 drug Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
208000000718 duodenal ulcer Diseases 0.000 description 1
239000002895 emetic Substances 0.000 description 1
230000000095 emetic effect Effects 0.000 description 1
239000012259 ether extract Substances 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
150000002240 furans Chemical class 0.000 description 1
239000007789 gas Substances 0.000 description 1
231100000029 gastro-duodenal ulcer Toxicity 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
125000000623 heterocyclic group Chemical group 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
239000000543 intermediate Substances 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
231100001231 less toxic Toxicity 0.000 description 1
231100000636 lethal dose Toxicity 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
239000012280 lithium aluminium hydride Substances 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
238000003760 magnetic stirring Methods 0.000 description 1
JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
239000012454 non-polar solvent Substances 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
HCTVWSOKIJULET-LQDWTQKMSA-M phenoxymethylpenicillin potassium Chemical compound [K+].N([C@H]1[C@H]2SC([C@@H](N2C1=O)C([O-])=O)(C)C)C(=O)COC1=CC=CC=C1 HCTVWSOKIJULET-LQDWTQKMSA-M 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
239000006187 pill Substances 0.000 description 1
239000004089 psychotropic agent Substances 0.000 description 1
150000003222 pyridines Chemical class 0.000 description 1
239000013558 reference substance Substances 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
238000007157 ring contraction reaction Methods 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
RBWSWDPRDBEWCR-RKJRWTFHSA-N sodium;(2r)-2-[(2r)-3,4-dihydroxy-5-oxo-2h-furan-2-yl]-2-hydroxyethanolate Chemical compound [Na+].[O-]C[C@@H](O)[C@H]1OC(=O)C(O)=C1O RBWSWDPRDBEWCR-RKJRWTFHSA-N 0.000 description 1
239000012265 solid product Substances 0.000 description 1
241000894007 species Species 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
238000012453 sprague-dawley rat model Methods 0.000 description 1
230000035882 stress Effects 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
229910021653 sulphate ion Inorganic materials 0.000 description 1
239000000829 suppository Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000003826 tablet Substances 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
JCMLRUNDSXARRW-UHFFFAOYSA-N trioxouranium Chemical compound O=[U](=O)=O JCMLRUNDSXARRW-UHFFFAOYSA-N 0.000 description 1
238000005406 washing Methods 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
- C07D207/263—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms
- C07D207/27—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—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
- 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
- C07D207/20—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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 or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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 or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/26—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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 or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by nitrogen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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
- C07D211/70—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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
- C07D211/72—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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, directly attached to ring carbon atoms
- C07D211/74—Oxygen atoms
- C07D211/76—Oxygen atoms attached in position 2 or 6

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pyrrole Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Medicinal Preparation (AREA)

CA241,723A 1974-12-18 1975-12-15 Synthese de derives de methoxy-2 benzamide Expired CA1039731A (fr)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
FR7441718A FR2294698A1 (fr)	1974-12-18	1974-12-18	Nouveaux derives des methoxy-2 benzamides substitues, leurs sels, leur preparation et les medicaments qui en renferment
FR7531334A FR2327771A2 (fr)	1975-10-14	1975-10-14	Nouveaux derives des methoxy-2 benzamides substitues, leurs sels, leur preparation et les medicaments qui en renferment
FR7534570A FR2331345A2 (fr)	1975-11-13	1975-11-13	Nouveaux derives des methoxy-2 benzamides substitues, leurs sels, leur preparation et les medicaments qui en renferment

Publications (1)

Publication Number	Publication Date
CA1039731A true CA1039731A (fr)	1978-10-03

Family

ID=27250393

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA241,723A Expired CA1039731A (fr)	1974-12-18	1975-12-15	Synthese de derives de methoxy-2 benzamide

Country Status (17)

Country	Link
AT (1)	AT353782B (fr)
AU (1)	AU497616B2 (fr)
CA (1)	CA1039731A (fr)
CH (1)	CH612668A5 (fr)
DE (1)	DE2556457C3 (fr)
DK (1)	DK574075A (fr)
ES (2)	ES443563A1 (fr)
FI (1)	FI753586A7 (fr)
GB (1)	GB1508880A (fr)
GR (1)	GR59205B (fr)
IE (1)	IE42210B1 (fr)
IL (1)	IL48678A (fr)
LU (1)	LU74026A1 (fr)
MX (1)	MX3180E (fr)
NL (1)	NL168219C (fr)
NO (1)	NO143625C (fr)
SE (1)	SE412908B (fr)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4189495A (en) *	1974-09-17	1980-02-19	Synthelabo	2-Methoxy-benzamide derivatives
US4097481A (en) *	1976-11-08	1978-06-27	Riker Laboratories, Inc.	Tertiary amide derivatives of pyrrolidine and piperidine
FR2415099A1 (fr) *	1978-01-20	1979-08-17	Ile De France	Nouveaux derives de 4-amino-5-alkylsulfonyl ortho-anisamides, leurs procedes de preparation et leur application comme psychotropes
FR2440946A2 (fr) *	1978-01-20	1980-06-06	Ile De France	Nouveaux benzamides heterocycliques substitues, leurs procedes de preparation et leur application comme modificateurs du comportement
SE411118B (sv) *	1978-03-23	1979-12-03	Astra Laekemedel Ab	Ett forfarande for framstellning av 2,6-dialkoxibensamider med terapentiska egenskaper
SE8101536L (sv) *	1981-03-11	1982-09-12	Astra Laekemedel Ab	Bensamid-derivat
SE8205135D0 (sv) *	1982-09-09	1982-09-09	Astra Laekemedel Ab	Benzamido-derivatives
IL109422A0 (en) *	1993-04-30	1994-07-31	Shell Int Research	N-benzyl heterocyclic compounds, process for their preparation and pesticidal compositions containing them
EP0623601A1 (fr) *	1993-04-30	1994-11-09	Shell Internationale Researchmaatschappij B.V.	Dérivés hétérocycliques N-(3-fluorobenzyles) et leur utilisation comme pesticides
CA2355296A1 (fr) *	1998-12-11	2000-06-15	American Biogenetic Sciences, Inc.	Composes heterocycliques azotes substitues et leur utilisation therapeutique

1975
- 1975-12-15 IE IE2731/75A patent/IE42210B1/en unknown
- 1975-12-15 SE SE7514143A patent/SE412908B/xx unknown
- 1975-12-15 CA CA241,723A patent/CA1039731A/fr not_active Expired
- 1975-12-15 DE DE2556457A patent/DE2556457C3/de not_active Expired
- 1975-12-16 IL IL48678A patent/IL48678A/xx unknown
- 1975-12-16 LU LU74026A patent/LU74026A1/xx unknown
- 1975-12-16 NO NO754284A patent/NO143625C/no unknown
- 1975-12-16 NL NLAANVRAGE7514620,A patent/NL168219C/xx not_active IP Right Cessation
- 1975-12-17 AU AU87646/75A patent/AU497616B2/en not_active Expired
- 1975-12-17 DK DK574075A patent/DK574075A/da not_active Application Discontinuation
- 1975-12-17 GR GR49632A patent/GR59205B/el unknown
- 1975-12-17 ES ES75443563A patent/ES443563A1/es not_active Expired
- 1975-12-17 AT AT959075A patent/AT353782B/de active
- 1975-12-17 MX MX001641U patent/MX3180E/es unknown
- 1975-12-17 GB GB51635/75A patent/GB1508880A/en not_active Expired
- 1975-12-18 FI FI753586A patent/FI753586A7/fi not_active Application Discontinuation
- 1975-12-18 CH CH1641375A patent/CH612668A5/xx not_active IP Right Cessation
1977
- 1977-04-15 ES ES457872A patent/ES457872A1/es not_active Expired

Also Published As

Publication number	Publication date
CH612668A5 (fr)	1979-08-15
IE42210L (en)	1976-06-18
ES457872A1 (es)	1978-03-01
ES443563A1 (es)	1977-08-16
ATA959075A (de)	1979-05-15
NO754284L (fr)	1976-06-21
DE2556457C3 (de)	1981-02-12
DK574075A (da)	1976-06-19
SE7514143L (sv)	1976-06-21
AU8764675A (en)	1977-06-23
NL168219B (nl)	1981-10-16
MX3180E (es)	1980-06-11
NO143625B (no)	1980-12-08
NL168219C (nl)	1982-03-16
GR59205B (en)	1977-11-26
IL48678A0 (en)	1976-02-29
NO143625C (no)	1981-03-18
DE2556457B2 (de)	1980-05-29
GB1508880A (en)	1978-04-26
IE42210B1 (en)	1980-06-18
AT353782B (de)	1979-12-10
SE412908B (sv)	1980-03-24
AU497616B2 (en)	1978-12-21
IL48678A (en)	1979-01-31
LU74026A1 (fr)	1976-11-11
NL7514620A (nl)	1976-06-22
DE2556457A1 (de)	1976-06-24
FI753586A7 (fr)	1976-06-19

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US5885985A (en)	1999-03-23	Guanidine derivatives useful in therapy
PT93689B (pt)	1996-06-28	Processo para a preparacao de benzimidazois e de composicoes farmaceuticas que os contem
KR20140070550A (ko)	2014-06-10	항암제로서의 삼환식 화합물
US4361562A (en)	1982-11-30	3-Aminopropoxyaryl derivatives, their preparation and pharmaceutical compositions containing them
KR100904829B1 (ko)	2009-06-25	4-아미노피페리딘 유도체
WO2002089793A1 (fr)	2002-11-14	Sulfonamides
US4021567A (en)	1977-05-03	2-Methoxy-benzamide derivatives
CA1273929A (fr)	1990-09-11	N-(piperidinylaklyl) carboxamides
AU682768B2 (en)	1997-10-16	Bicyclic amidine derivatives as inhibitors of nitric oxide synthetase
US4904663A (en)	1990-02-27	N-(2-oxpyrrolidin-1-yl-)acetyl)piperazine derivatives and drug for senile dementia
IE882179L (en)	1989-01-16	N,n-disubstituted arylamides
GB1585133A (en)	1981-02-25	Derivatives of perhydro-aza-heterocycles and processes for the production thereof
US4189495A (en)	1980-02-19	2-Methoxy-benzamide derivatives
IE42210B1 (en)	1980-06-18	2-methoxy-benzamide derivatives
CA1254561A (fr)	1989-05-23	Composes a base de 3-aminocarbonylmethoxy-5- phenylpyrazole; methode de preparation et compositions pharmaceutiques a base de ces composes
US4158060A (en)	1979-06-12	2-Methoxy-benzamide derivatives
US3813387A (en)	1974-05-28	Sulphamoylphenyl pyrrolidinones
SK16896A3 (en)	1996-10-02	1-£2-(substituted vinyl)\|-3,4-dihydro-5h-2,3-benzodiazepine derivatives
CA2081147A1 (fr)	1993-04-24	Derives du naphtamide, leur procede de preparation et leur application dans le domaine therapeutique
KR900009007B1 (ko)	1990-12-17	치환 아자비사이클로알칸의 제조방법
AU645917B2 (en)	1994-01-27	New N-(isoquinolin-5-ylsulphonyl)azacycloalkanes, process for the preparation thereof, and pharmaceutical compositions containing them
US4172143A (en)	1979-10-23	2-Methoxy-benzamide derivatives
US6127362A (en)	2000-10-03	9,10-diazatricyclo[4,4,1,12,5 ] decane and 2,7-diazatricyclo [4,4,0,03,8 ] decane derivatives having analgesic activity
US3154557A (en)	1964-10-27	2[omega-(2- and 4-pyridyl)-lower-alkoxy]tetrahydropyrans and compounds prepared therefrom