CH507202A - Verfahren zur Herstellung von basischen Äthern - Google Patents

Verfahren zur Herstellung von basischen Äthern

Info

Publication number: CH507202A
Authority: CH; Switzerland
Prior art keywords: formula; benzyl; cycloheptane; group; fumarate
Prior art date: 1966-01-15

Application number

CH46267A

Other languages

German (de)

English (en)

Inventor

Laszlo Dr Pallos

Zolyomi Gabor

Budai Zoltan

Original Assignee

Egyt Gyogyszervegyeszeti Gyar

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.)

1966-01-15

Filing date

1967-01-12

Publication date

1971-05-15

1967-01-12 Application filed by Egyt Gyogyszervegyeszeti Gyar filed Critical Egyt Gyogyszervegyeszeti Gyar

1971-05-15 Publication of CH507202A publication Critical patent/CH507202A/de

Links

150000002170 ethers Chemical class 0.000 title claims abstract description 16
230000002093 peripheral effect Effects 0.000 title abstract description 4
230000000304 vasodilatating effect Effects 0.000 title abstract description 4
GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 title abstract description 3
230000003444 anaesthetic effect Effects 0.000 title abstract description 3
230000001387 anti-histamine Effects 0.000 title abstract description 3
239000000739 antihistaminic agent Substances 0.000 title abstract description 3
230000002048 spasmolytic effect Effects 0.000 title description 4
239000000812 cholinergic antagonist Substances 0.000 title description 2
125000004122 cyclic group Chemical group 0.000 title description 2
150000001298 alcohols Chemical class 0.000 title 1
239000002253 acid Substances 0.000 claims abstract description 18
150000003839 salts Chemical class 0.000 claims abstract description 15
125000000217 alkyl group Chemical group 0.000 claims abstract description 13
229910052736 halogen Inorganic materials 0.000 claims abstract description 10
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 7
125000003545 alkoxy group Chemical group 0.000 claims abstract description 6
125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 6
229910052783 alkali metal Inorganic materials 0.000 claims abstract description 5
150000001340 alkali metals Chemical group 0.000 claims abstract description 5
125000005041 acyloxyalkyl group Chemical group 0.000 claims abstract description 4
125000003282 alkyl amino group Chemical group 0.000 claims abstract description 4
125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 4
150000002367 halogens Chemical class 0.000 claims abstract description 4
125000005842 heteroatom Chemical group 0.000 claims abstract description 4
125000004950 trifluoroalkyl group Chemical group 0.000 claims abstract description 4
-1 1-Benzyl-1- (3'-diethylamino-ethylaminopropoxy) -cycloheptane fumarate Chemical compound 0.000 claims description 59
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 54
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 42
150000001875 compounds Chemical class 0.000 claims description 39
238000000034 method Methods 0.000 claims description 38
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 30
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 27
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 18
150000002148 esters Chemical class 0.000 claims description 16
239000000203 mixture Substances 0.000 claims description 13
150000001412 amines Chemical class 0.000 claims description 11
239000011541 reaction mixture Substances 0.000 claims description 11
238000006243 chemical reaction Methods 0.000 claims description 9
239000002904 solvent Substances 0.000 claims description 9
150000004820 halides Chemical class 0.000 claims description 8
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 7
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 7
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 6
125000002252 acyl group Chemical group 0.000 claims description 6
238000002360 preparation method Methods 0.000 claims description 6
239000000047 product Substances 0.000 claims description 6
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 claims description 6
238000003756 stirring Methods 0.000 claims description 6
238000001704 evaporation Methods 0.000 claims description 5
230000008020 evaporation Effects 0.000 claims description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
239000011777 magnesium Substances 0.000 claims description 5
229910052749 magnesium Inorganic materials 0.000 claims description 5
150000002736 metal compounds Chemical class 0.000 claims description 5
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 5
125000001424 substituent group Chemical group 0.000 claims description 5
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 5
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims description 4
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 4
230000010933 acylation Effects 0.000 claims description 4
238000005917 acylation reaction Methods 0.000 claims description 4
150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 4
239000003054 catalyst Substances 0.000 claims description 4
239000007795 chemical reaction product Substances 0.000 claims description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 4
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 description 3
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 3
235000019270 ammonium chloride Nutrition 0.000 claims description 3
125000004432 carbon atom Chemical group C* 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 3
239000001257 hydrogen Substances 0.000 claims description 3
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 3
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
229920006395 saturated elastomer Polymers 0.000 claims description 3
229910052708 sodium Inorganic materials 0.000 claims description 3
239000011734 sodium Substances 0.000 claims description 3
235000017557 sodium bicarbonate Nutrition 0.000 claims description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 3
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 2
BUHYMJLFRZAFBF-UHFFFAOYSA-N 3,4,5-trimethoxybenzoyl chloride Chemical compound COC1=CC(C(Cl)=O)=CC(OC)=C1OC BUHYMJLFRZAFBF-UHFFFAOYSA-N 0.000 claims description 2
LSTKNZAMFRGXCG-WLHGVMLRSA-N Bencyclane fumarate Chemical compound OC(=O)\C=C\C(O)=O.C=1C=CC=CC=1CC1(OCCCN(C)C)CCCCCC1 LSTKNZAMFRGXCG-WLHGVMLRSA-N 0.000 claims description 2
DBRRSASGAUSKDP-UHFFFAOYSA-N C1CCCCCC1.OC(=O)C=CC(O)=O Chemical compound C1CCCCCC1.OC(=O)C=CC(O)=O DBRRSASGAUSKDP-UHFFFAOYSA-N 0.000 claims description 2
230000002378 acidificating effect Effects 0.000 claims description 2
150000001408 amides Chemical class 0.000 claims description 2
239000011230 binding agent Substances 0.000 claims description 2
125000006842 cycloalkyleneimino group Chemical group 0.000 claims description 2
238000000354 decomposition reaction Methods 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
150000004678 hydrides Chemical class 0.000 claims description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 2
238000011065 in-situ storage Methods 0.000 claims description 2
230000007935 neutral effect Effects 0.000 claims description 2
229910052757 nitrogen Inorganic materials 0.000 claims description 2
125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims description 2
229910000027 potassium carbonate Inorganic materials 0.000 claims description 2
235000009518 sodium iodide Nutrition 0.000 claims description 2
230000001419 dependent effect Effects 0.000 claims 4
125000002015 acyclic group Chemical group 0.000 claims 1
125000003277 amino group Chemical group 0.000 claims 1
229930007927 cymene Natural products 0.000 claims 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims 1
239000003960 organic solvent Substances 0.000 claims 1
HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Chemical compound CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 0.000 claims 1
238000004519 manufacturing process Methods 0.000 abstract description 6
125000004429 atom Chemical group 0.000 abstract description 2
125000002947 alkylene group Chemical group 0.000 abstract 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
125000001453 quaternary ammonium group Chemical group 0.000 abstract 1
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 8
230000015572 biosynthetic process Effects 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
238000003786 synthesis reaction Methods 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
239000012074 organic phase Substances 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
230000000694 effects Effects 0.000 description 4
XQYZDYMELSJDRZ-UHFFFAOYSA-N papaverine Chemical compound C1=C(OC)C(OC)=CC=C1CC1=NC=CC2=CC(OC)=C(OC)C=C12 XQYZDYMELSJDRZ-UHFFFAOYSA-N 0.000 description 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
JOXIMZWYDAKGHI-UHFFFAOYSA-N p-toluenesulfonic acid Substances CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
238000000746 purification Methods 0.000 description 3
238000005292 vacuum distillation Methods 0.000 description 3
229930008281 A03AD01 - Papaverine Natural products 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
239000003513 alkali Substances 0.000 description 2
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
238000010533 azeotropic distillation Methods 0.000 description 2
238000009835 boiling Methods 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
238000001816 cooling Methods 0.000 description 2
RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
238000004821 distillation Methods 0.000 description 2
238000006266 etherification reaction Methods 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
238000002955 isolation Methods 0.000 description 2
229910052744 lithium Inorganic materials 0.000 description 2
239000003589 local anesthetic agent Substances 0.000 description 2
JKQOBWVOAYFWKG-UHFFFAOYSA-N molybdenum trioxide Chemical compound O=[Mo](=O)=O JKQOBWVOAYFWKG-UHFFFAOYSA-N 0.000 description 2
229960001789 papaverine Drugs 0.000 description 2
239000012429 reaction media Substances 0.000 description 2
238000010992 reflux Methods 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
239000008096 xylene Substances 0.000 description 2
WDXYVJKNSMILOQ-UHFFFAOYSA-N 1,3,2-dioxathiolane 2-oxide Chemical compound O=S1OCCO1 WDXYVJKNSMILOQ-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
IJDXSTIWUARVEK-UHFFFAOYSA-N 1,4-dioxaspiro[4.4]nonane Chemical compound C1CCCC21OCCO2 IJDXSTIWUARVEK-UHFFFAOYSA-N 0.000 description 1
GZGPRZYZKBQPBQ-UHFFFAOYSA-N 1,4-dioxaspiro[4.5]decane Chemical compound O1CCOC11CCCCC1 GZGPRZYZKBQPBQ-UHFFFAOYSA-N 0.000 description 1
SDDZRHXHMJURQC-UHFFFAOYSA-N 1,4-dioxaspiro[4.7]dodecane Chemical compound O1CCOC11CCCCCCC1 SDDZRHXHMJURQC-UHFFFAOYSA-N 0.000 description 1
LSDTWMHYCLFXBZ-UHFFFAOYSA-N 1,5-dioxaspiro[5.5]undecane Chemical compound C1CCCCC21OCCCO2 LSDTWMHYCLFXBZ-UHFFFAOYSA-N 0.000 description 1
GHTNEJJXVUMOPX-UHFFFAOYSA-N 2-[1-(4-chlorophenyl)cyclohexyl]oxy-n,n-diethylethanamine;hydrochloride Chemical compound [Cl-].C=1C=C(Cl)C=CC=1C1(OCC[NH+](CC)CC)CCCCC1 GHTNEJJXVUMOPX-UHFFFAOYSA-N 0.000 description 1
UZKBWDBOLMCCLQ-UHFFFAOYSA-N 3-(1-benzylcycloheptyl)oxypropan-1-ol Chemical compound C(C1=CC=CC=C1)C1(CCCCCC1)OCCCO UZKBWDBOLMCCLQ-UHFFFAOYSA-N 0.000 description 1
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
NNJVILVZKWQKPM-UHFFFAOYSA-N Lidocaine Chemical compound CCN(CC)CC(=O)NC1=C(C)C=CC=C1C NNJVILVZKWQKPM-UHFFFAOYSA-N 0.000 description 1
LZBMDFQSONQUDI-UHFFFAOYSA-N OCCCOC1(CCCCC1)C(C=C1)=CC=C1Cl Chemical compound OCCCOC1(CCCCC1)C(C=C1)=CC=C1Cl LZBMDFQSONQUDI-UHFFFAOYSA-N 0.000 description 1
OLDSLRNKZOEHFJ-UHFFFAOYSA-N OCCOC1(CC(C=C2)=CC=C2Cl)CCCCC1 Chemical compound OCCOC1(CC(C=C2)=CC=C2Cl)CCCCC1 OLDSLRNKZOEHFJ-UHFFFAOYSA-N 0.000 description 1
HYKSLXPZSCWDCK-UHFFFAOYSA-N OCCOC1(CC(C=C2)=CC=C2Cl)CCCCCC1 Chemical compound OCCOC1(CC(C=C2)=CC=C2Cl)CCCCCC1 HYKSLXPZSCWDCK-UHFFFAOYSA-N 0.000 description 1
JLDCHZDOTGGJCW-UHFFFAOYSA-N OCCOC1(CC(C=C2)=CC=C2Cl)CCCCCCC1 Chemical compound OCCOC1(CC(C=C2)=CC=C2Cl)CCCCCCC1 JLDCHZDOTGGJCW-UHFFFAOYSA-N 0.000 description 1
MJPJTQUYERZJEY-UHFFFAOYSA-N OCCOC1(CCCCC1)C(C=C1)=CC=C1Cl Chemical compound OCCOC1(CCCCC1)C(C=C1)=CC=C1Cl MJPJTQUYERZJEY-UHFFFAOYSA-N 0.000 description 1
208000027089 Parkinsonian disease Diseases 0.000 description 1
206010034010 Parkinsonism Diseases 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
208000025865 Ulcer Diseases 0.000 description 1
238000006959 Williamson synthesis reaction Methods 0.000 description 1
VIWMRMDXMRQPGZ-UHFFFAOYSA-N [1-(1-phenylcyclohexyl)oxycyclohexyl]benzene Chemical class C1CCCCC1(C=1C=CC=CC=1)OC1(C=2C=CC=CC=2)CCCCC1 VIWMRMDXMRQPGZ-UHFFFAOYSA-N 0.000 description 1
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
150000004703 alkoxides Chemical class 0.000 description 1
150000001350 alkyl halides Chemical class 0.000 description 1
125000004414 alkyl thio group Chemical group 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
UKFWSNCTAHXBQN-UHFFFAOYSA-N ammonium iodide Chemical compound [NH4+].[I-] UKFWSNCTAHXBQN-UHFFFAOYSA-N 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
230000036772 blood pressure Effects 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000000969 carrier Substances 0.000 description 1
210000003169 central nervous system Anatomy 0.000 description 1
239000002026 chloroform extract Substances 0.000 description 1
239000012043 crude product Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
150000001924 cycloalkanes Chemical class 0.000 description 1
239000000284 extract Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
238000004508 fractional distillation Methods 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000003502 gasoline Substances 0.000 description 1
BCDGQXUMWHRQCB-UHFFFAOYSA-N glycine methyl ketone Natural products CC(=O)CN BCDGQXUMWHRQCB-UHFFFAOYSA-N 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
229910001385 heavy metal Inorganic materials 0.000 description 1
XLYOFNOQVPJJNP-ZSJDYOACSA-N heavy water Substances [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
239000012433 hydrogen halide Substances 0.000 description 1
229910000039 hydrogen halide Inorganic materials 0.000 description 1
239000005457 ice water Substances 0.000 description 1
125000001841 imino group Chemical group [H]N=* 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
238000011835 investigation Methods 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical class II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
150000002497 iodine compounds Chemical class 0.000 description 1
239000003456 ion exchange resin Substances 0.000 description 1
229920003303 ion-exchange polymer Polymers 0.000 description 1
238000006317 isomerization reaction Methods 0.000 description 1
229960004194 lidocaine Drugs 0.000 description 1
239000007788 liquid Substances 0.000 description 1
150000002642 lithium compounds Chemical class 0.000 description 1
238000011866 long-term treatment Methods 0.000 description 1
TWXDDNPPQUTEOV-FVGYRXGTSA-N methamphetamine hydrochloride Chemical compound Cl.CN[C@@H](C)CC1=CC=CC=C1 TWXDDNPPQUTEOV-FVGYRXGTSA-N 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
125000005489 p-toluenesulfonic acid group Chemical class 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
239000012071 phase Substances 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
230000001624 sedative effect Effects 0.000 description 1
210000002966 serum Anatomy 0.000 description 1
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
KVCGISUBCHHTDD-UHFFFAOYSA-M sodium;4-methylbenzenesulfonate Chemical compound [Na+].CC1=CC=C(S([O-])(=O)=O)C=C1 KVCGISUBCHHTDD-UHFFFAOYSA-M 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000397 ulcer Toxicity 0.000 description 1

Classifications

- 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
- C07D295/08—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 bound oxygen or sulfur atoms
- C07D295/084—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 bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—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 bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof

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

CH46267A 1966-01-15 1967-01-12 Verfahren zur Herstellung von basischen Äthern CH507202A (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
HUEE001219		1966-01-15

Publications (1)

Publication Number	Publication Date
CH507202A true CH507202A (de)	1971-05-15

Family

ID=10995186

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH46267A CH507202A (de)	1966-01-15	1967-01-12	Verfahren zur Herstellung von basischen Äthern

Country Status (9)

Country	Link
AT (1)	AT271426B (cs)
CH (1)	CH507202A (cs)
CS (1)	CS152439B2 (cs)
DE (2)	DE1792788A1 (cs)
DK (1)	DK137570B (cs)
FR (1)	FR1511193A (cs)
NL (1)	NL153871B (cs)
SE (1)	SE337369B (cs)
YU (1)	YU34391B (cs)

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE1094738B (de) *	1959-09-03	1960-12-15	Boehringer & Soehne Gmbh	Verfahren zur Herstellung neuer, auf das Zentralnervensystem hemmend wirkender basischer AEther, deren Salzen und quaternaeren Ammoniumverbindungen
AT264495B (de) *	1963-08-18	1968-09-10	Egyt Gyogyszervegyeszeti Gyar	Verfahren zur Herstellung von neuen basischen Cycloheptanoläthern

1967
- 1967-01-10 DE DE19671792788 patent/DE1792788A1/de not_active Ceased
- 1967-01-10 DE DE1967E0033182 patent/DE1618297B2/de active Granted
- 1967-01-12 CH CH46267A patent/CH507202A/de not_active IP Right Cessation
- 1967-01-13 NL NL6700592A patent/NL153871B/xx not_active IP Right Cessation
- 1967-01-13 YU YU5467A patent/YU34391B/xx unknown
- 1967-01-13 DK DK21367A patent/DK137570B/da not_active IP Right Cessation
- 1967-01-13 SE SE54267A patent/SE337369B/xx unknown
- 1967-01-13 AT AT35367A patent/AT271426B/de active
- 1967-01-13 FR FR91112A patent/FR1511193A/fr not_active Expired
- 1967-01-16 CS CS35467A patent/CS152439B2/cs unknown

Also Published As

Publication number	Publication date
YU34391B (en)	1979-07-10
NL6700592A (cs)	1967-07-17
DE1792788A1 (de)	1976-10-21
YU5467A (en)	1978-12-31
FR1511193A (fr)	1968-01-26
DK137570C (cs)	1978-09-11
SE337369B (cs)	1971-08-09
AT271426B (de)	1969-06-10
DE1618297A1 (de)	1972-05-04
DK137570B (da)	1978-03-28
CS152439B2 (cs)	1973-12-19
DE1618297B2 (de)	1976-07-08
NL153871B (nl)	1977-07-15

Legal Events

Date	Code	Title	Description
1987-03-31	PL	Patent ceased

Publication	Publication Date	Title
DD270529A5 (de)	1989-08-02	Verfahren zur herstellung von naphthalinderivaten
DE2334404C2 (de)	1982-10-28	Alkylthiophenyl-2-n-octylaminoalkohole und deren Salze, Verfahren zu deren Herstellung und pharmazeutische Zubereitung
DE69023906T2 (de)	1996-04-11	Benzopyrane und Verfahren zu deren Herstellung.
DE2229035A1 (de)	1972-12-21	Cyclopentanderivate
DE2456959A1 (de)	1976-06-16	4-(e)- und 4-(z)-7-methyl-9-(2,6,6trimethyl-1-cyclohexen-1-yl)-nona-2,4,6,8tetraencarbonsaeure, ihre derivate und diese enthaltende zubereitungen
DE2929760C2 (cs)	1987-05-27
DE3025238A1 (de)	1981-03-26	Basische cycloalkanonoximaether, verfahren zur herstellung derselben und diese enthaltende arzneimittel
CH507202A (de)	1971-05-15	Verfahren zur Herstellung von basischen Äthern
DE2704690C2 (de)	1987-01-29	Triphenylalkenderivate, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel
DE1618297C3 (de)	1977-03-10	Verfahren zur Herstellung von basischen Äthern
DE2462966C2 (de)	1983-12-29	Derivate des 3-Amino-4-acetyl-5-methylpyrrols und diese enthaltende pharmazeutische Zubereitungen
CH493467A (de)	1970-07-15	Verfahren zur Herstellung von Dibenzosuberenderivaten
EP0004260B1 (de)	1980-10-29	Substituierte Chinolizidin- und Indolizidinmethanolderivate, Verfahren zur Herstellung derselben und Arzneimittel, welche diese enthalten
DE959825C (de)	1957-03-14	Verfahren zur Herstellung von in 2-Stellung endocyclisch substituierten 2, 3-Dihydro-enzo-1, 3-oxazonen-(4)
AT256816B (de)	1967-09-11	Verfahren zur Herstellung von neuen substituierten 1-Phenyl-2-aminoalkanolen und deren Säureadditionssalzen
DE2822473C2 (de)	1987-01-08	Alkanolaminderivate und pharmazeutische Mittel, welche diese Alkanolaminderivate enthalten
EP0158312B1 (de)	1990-09-12	1-[Cyclohexyl]-3,4-di-[hydro]-isochinolinderivate, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel
DD251339A5 (de)	1987-11-11	Verfahren zur herstellung von neuen phenolderivaten
DE1443813A1 (de)	1968-11-28	Verfahren zur Herstellung von neuen basischen Cycloalkanol-AEthern
DE3141819C2 (cs)	1989-08-10
DE2261269A1 (de)	1973-06-28	Arylketone, verfahren zu ihrer herstellung und ihre verwendung in arzneimitteln
DE3442365A1 (de)	1985-06-05	Neue azabicyclische verbindungen und verfahren zu deren herstellung
DE1643928C3 (de)	1975-09-18	Verfahren zur Herstellung von Alkylaminoalkyläthern von Cycloalkanolen
AT343106B (de)	1978-05-10	Verfahren zur herstellung von neuen aminoalkylestern von indanylcarbonsauren
DE1182237B (de)	1964-11-26	Verfahren zur Herstellung von 10-[4'-Hydroxy-4'-hydroxyalkylpiperidinoalkyl]-phenthiazin-derivaten