CA1252104A - COMPOSES D'AMINOMETHYLTRIORGANOTINE, .alpha.-MONO OU DISUBSTITUES ET METHODE DE PREPARATION - Google Patents

COMPOSES D'AMINOMETHYLTRIORGANOTINE, .alpha.-MONO OU DISUBSTITUES ET METHODE DE PREPARATION

Info

Publication number: CA1252104A
Authority: CA; Canada
Prior art keywords: hydrogen; together form; compound; carbon atoms; compounds
Prior art date: 1984-06-22
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

CA000457175A

Other languages

English (en)

Inventor

Bernard Elissondo

Michel Pereyre

Jean-Paul Quintard

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.)

Centre National de la Recherche Scientifique CNRS

Original Assignee

Centre National de la Recherche Scientifique CNRS

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.)

1984-06-22

Filing date

1984-06-22

Publication date

1989-04-04

1984-06-22 Application filed by Centre National de la Recherche Scientifique CNRS filed Critical Centre National de la Recherche Scientifique CNRS

1984-06-22 Priority to CA000457175A priority Critical patent/CA1252104A/fr

1989-04-04 Application granted granted Critical

1989-04-04 Publication of CA1252104A publication Critical patent/CA1252104A/fr

Status Expired legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 59
238000000034 method Methods 0.000 title claims abstract description 44
238000002360 preparation method Methods 0.000 title claims abstract description 18
229910052739 hydrogen Inorganic materials 0.000 claims description 24
239000001257 hydrogen Substances 0.000 claims description 23
125000004432 carbon atom Chemical group C* 0.000 claims description 15
229910052751 metal Inorganic materials 0.000 claims description 15
239000002184 metal Substances 0.000 claims description 15
239000000460 chlorine Substances 0.000 claims description 12
125000000623 heterocyclic group Chemical group 0.000 claims description 12
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 11
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
125000000753 cycloalkyl group Chemical group 0.000 claims description 7
150000002431 hydrogen Chemical group 0.000 claims description 7
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
125000002541 furyl group Chemical group 0.000 claims description 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
229920006395 saturated elastomer Polymers 0.000 claims description 6
125000003118 aryl group Chemical group 0.000 claims description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
229910052744 lithium Inorganic materials 0.000 claims description 5
239000000203 mixture Substances 0.000 claims description 5
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 4
229910052736 halogen Inorganic materials 0.000 claims description 4
150000002902 organometallic compounds Chemical class 0.000 claims description 4
125000002723 alicyclic group Chemical group 0.000 claims description 3
125000001931 aliphatic group Chemical group 0.000 claims description 3
229910052801 chlorine Inorganic materials 0.000 claims description 3
125000001309 chloro group Chemical group Cl* 0.000 claims description 3
150000002367 halogens Chemical group 0.000 claims description 3
229910052700 potassium Inorganic materials 0.000 claims description 3
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
229910052794 bromium Inorganic materials 0.000 claims description 2
229910052740 iodine Chemical group 0.000 claims description 2
229910052708 sodium Inorganic materials 0.000 claims description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 8
125000004433 nitrogen atom Chemical group N* 0.000 claims 6
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 5
125000003386 piperidinyl group Chemical group 0.000 claims 4
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 2
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 claims 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
239000011630 iodine Chemical group 0.000 claims 1
239000011591 potassium Substances 0.000 claims 1
239000011734 sodium Substances 0.000 claims 1
230000015572 biosynthetic process Effects 0.000 abstract description 12
238000003786 synthesis reaction Methods 0.000 abstract description 12
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 abstract description 10
150000007975 iminium salts Chemical class 0.000 abstract description 9
150000003606 tin compounds Chemical class 0.000 abstract description 5
230000000144 pharmacologic effect Effects 0.000 abstract description 2
238000001228 spectrum Methods 0.000 abstract description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical class CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 19
238000006243 chemical reaction Methods 0.000 description 19
-1 amino-methyl organometallic compounds Chemical class 0.000 description 11
150000003254 radicals Chemical class 0.000 description 10
229910052718 tin Inorganic materials 0.000 description 10
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
241001269238 Data Species 0.000 description 5
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 5
238000009835 boiling Methods 0.000 description 5
229910052757 nitrogen Inorganic materials 0.000 description 5
239000000376 reactant Substances 0.000 description 5
150000003839 salts Chemical class 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
150000001414 amino alcohols Chemical class 0.000 description 4
239000007795 chemical reaction product Substances 0.000 description 4
239000002904 solvent Substances 0.000 description 4
239000007858 starting material Substances 0.000 description 4
125000001424 substituent group Chemical group 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
FDMBBCOBEAVDAO-UHFFFAOYSA-N Stovaine Chemical compound CN(C)CC(C)(CC)OC(=O)C1=CC=CC=C1 FDMBBCOBEAVDAO-UHFFFAOYSA-N 0.000 description 3
CQNZJBBODISZHP-UHFFFAOYSA-M [Cl-].CCCC[Sn]([Mg+])(CCCC)CCCC Chemical compound [Cl-].CCCC[Sn]([Mg+])(CCCC)CCCC CQNZJBBODISZHP-UHFFFAOYSA-M 0.000 description 3
150000001299 aldehydes Chemical class 0.000 description 3
229960000806 amylocaine Drugs 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
150000003841 chloride salts Chemical class 0.000 description 3
150000002118 epoxides Chemical class 0.000 description 3
150000002170 ethers Chemical class 0.000 description 3
229940052303 ethers for general anesthesia Drugs 0.000 description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
239000000543 intermediate Substances 0.000 description 3
150000002576 ketones Chemical class 0.000 description 3
CVBZZPVPIVGEBX-UHFFFAOYSA-N n,n-dimethyl-1-tributylstannylmethanamine Chemical compound CCCC[Sn](CCCC)(CCCC)CN(C)C CVBZZPVPIVGEBX-UHFFFAOYSA-N 0.000 description 3
239000000126 substance Substances 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-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
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
KXFMRWMYDWIKMU-UHFFFAOYSA-N [Li]CN(C)C Chemical compound [Li]CN(C)C KXFMRWMYDWIKMU-UHFFFAOYSA-N 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
150000001450 anions Chemical class 0.000 description 2
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
229960004132 diethyl ether Drugs 0.000 description 2
150000002081 enamines Chemical class 0.000 description 2
125000005843 halogen group Chemical group 0.000 description 2
150000002642 lithium compounds Chemical class 0.000 description 2
CKVWBMJEETWJTF-UHFFFAOYSA-N lithium;tributyltin Chemical compound CCCC[Sn]([Li])(CCCC)CCCC CKVWBMJEETWJTF-UHFFFAOYSA-N 0.000 description 2
YAIPYAQVBZPSSC-UHFFFAOYSA-N macromerine Chemical compound COC1=CC=C(C(O)CN(C)C)C=C1OC YAIPYAQVBZPSSC-UHFFFAOYSA-N 0.000 description 2
238000005580 one pot reaction Methods 0.000 description 2
239000012429 reaction media Substances 0.000 description 2
238000010992 reflux Methods 0.000 description 2
125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 description 2
125000003638 stannyl group Chemical group [H][Sn]([H])([H])* 0.000 description 2
239000000758 substrate Substances 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
PSXLCTPHDAEPLK-UHFFFAOYSA-N CC(C)[Mg] Chemical compound CC(C)[Mg] PSXLCTPHDAEPLK-UHFFFAOYSA-N 0.000 description 1
241001133173 Hesiolyra bergi Species 0.000 description 1
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
229930013930 alkaloid Natural products 0.000 description 1
150000003797 alkaloid derivatives Chemical class 0.000 description 1
150000001336 alkenes Chemical class 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
238000006399 aminohydroxylation reaction Methods 0.000 description 1
125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 1
CHLWZORGKNCHAV-UHFFFAOYSA-N aminomethyltin Chemical compound NC[Sn] CHLWZORGKNCHAV-UHFFFAOYSA-N 0.000 description 1
244000309464 bull Species 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
230000000711 cancerogenic effect Effects 0.000 description 1
150000001768 cations Chemical class 0.000 description 1
238000002512 chemotherapy Methods 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
238000011109 contamination Methods 0.000 description 1
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
238000004821 distillation Methods 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000003480 eluent Substances 0.000 description 1
VVDUZZGYBOWDSQ-UHFFFAOYSA-M eschenmoser's salt Chemical compound [I-].C[N+](C)=C VVDUZZGYBOWDSQ-UHFFFAOYSA-M 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000012467 final product Substances 0.000 description 1
238000005755 formation reaction Methods 0.000 description 1
HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 1
239000011521 glass Substances 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
238000004811 liquid chromatography Methods 0.000 description 1
150000002641 lithium Chemical class 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
150000004005 nitrosamines Chemical class 0.000 description 1
150000002894 organic compounds Chemical class 0.000 description 1
150000002900 organolithium compounds Chemical class 0.000 description 1
125000001979 organolithium group Chemical group 0.000 description 1
125000002524 organometallic group Chemical group 0.000 description 1
150000003141 primary amines Chemical group 0.000 description 1
238000012545 processing Methods 0.000 description 1
239000001294 propane Substances 0.000 description 1
230000036647 reaction Effects 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
238000006884 silylation reaction Methods 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000012916 structural analysis Methods 0.000 description 1
230000002194 synthesizing effect Effects 0.000 description 1
FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 1
238000012360 testing method Methods 0.000 description 1
AFCAKJKUYFLYFK-UHFFFAOYSA-N tetrabutyltin Chemical compound CCCC[Sn](CCCC)(CCCC)CCCC AFCAKJKUYFLYFK-UHFFFAOYSA-N 0.000 description 1
ZUHZGEOKBKGPSW-UHFFFAOYSA-N tetraglyme Chemical compound COCCOCCOCCOCCOC ZUHZGEOKBKGPSW-UHFFFAOYSA-N 0.000 description 1
VXKWYPOMXBVZSJ-UHFFFAOYSA-N tetramethyltin Chemical compound C[Sn](C)(C)C VXKWYPOMXBVZSJ-UHFFFAOYSA-N 0.000 description 1
ATJFFYVFTNAWJD-IGMARMGPSA-N tin-119 atom Chemical compound [119Sn] ATJFFYVFTNAWJD-IGMARMGPSA-N 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000002110 toxicologic effect Effects 0.000 description 1
231100000027 toxicology Toxicity 0.000 description 1
238000012546 transfer Methods 0.000 description 1
238000006478 transmetalation reaction Methods 0.000 description 1
DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical compound CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 0.000 description 1
SYKYWNLSMURNCQ-UHFFFAOYSA-N tributylstannylmethanamine Chemical class CCCC[Sn](CN)(CCCC)CCCC SYKYWNLSMURNCQ-UHFFFAOYSA-N 0.000 description 1
238000005406 washing Methods 0.000 description 1

CA000457175A 1984-06-22 1984-06-22 COMPOSES D'AMINOMETHYLTRIORGANOTINE, .alpha.-MONO OU DISUBSTITUES ET METHODE DE PREPARATION Expired CA1252104A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000457175A CA1252104A (fr)	1984-06-22	1984-06-22	COMPOSES D'AMINOMETHYLTRIORGANOTINE, .alpha.-MONO OU DISUBSTITUES ET METHODE DE PREPARATION

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA000457175A CA1252104A (fr)	1984-06-22	1984-06-22	COMPOSES D'AMINOMETHYLTRIORGANOTINE, .alpha.-MONO OU DISUBSTITUES ET METHODE DE PREPARATION

Publications (1)

Publication Number	Publication Date
CA1252104A true CA1252104A (fr)	1989-04-04

Family

ID=4128147

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000457175A Expired CA1252104A (fr)	1984-06-22	1984-06-22	COMPOSES D'AMINOMETHYLTRIORGANOTINE, .alpha.-MONO OU DISUBSTITUES ET METHODE DE PREPARATION

Country Status (1)

Country	Link
CA (1)	CA1252104A (fr)

1984
- 1984-06-22 CA CA000457175A patent/CA1252104A/fr not_active Expired

Legal Events

Date	Code	Title	Description
2006-04-04	MKEX	Expiry
2023-05-26	MKEX	Expiry	Effective date: 20060404

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