CH388939A - Verfahren zur Herstellung neuer, auf das Zentralnervensystem hemmend wirkender, basischer Äther - Google Patents
Verfahren zur Herstellung neuer, auf das Zentralnervensystem hemmend wirkender, basischer ÄtherInfo
- Publication number
- CH388939A CH388939A CH862060A CH862060A CH388939A CH 388939 A CH388939 A CH 388939A CH 862060 A CH862060 A CH 862060A CH 862060 A CH862060 A CH 862060A CH 388939 A CH388939 A CH 388939A
- Authority
- CH
- Switzerland
- Prior art keywords
- new
- ether
- basic
- nervous system
- inhibit
- Prior art date
Links
- 150000002170 ethers Chemical class 0.000 title claims description 9
- 238000000034 method Methods 0.000 title claims description 5
- 210000003169 central nervous system Anatomy 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 150000003839 salts Chemical class 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
- -1 alkylene radical Chemical class 0.000 description 11
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- JSUAJTLKVREZHV-UHFFFAOYSA-N 1-[4-(1-pyrrolidinyl)but-2-ynyl]pyrrolidine Chemical compound C1CCCN1CC#CCN1CCCC1 JSUAJTLKVREZHV-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 210000000133 brain stem Anatomy 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- DGAUTSUNKGTRFC-UHFFFAOYSA-N 1-[(2-chlorophenyl)methyl]cyclohexan-1-ol Chemical compound C=1C=CC=C(Cl)C=1CC1(O)CCCCC1 DGAUTSUNKGTRFC-UHFFFAOYSA-N 0.000 description 1
- SCKDLDVPPKLCDR-UHFFFAOYSA-N 1-[(4-chlorophenyl)methyl]cycloheptan-1-ol Chemical compound C=1C=C(Cl)C=CC=1CC1(O)CCCCCC1 SCKDLDVPPKLCDR-UHFFFAOYSA-N 0.000 description 1
- RHDLCEUYNPSLDK-UHFFFAOYSA-N 1-[(4-chlorophenyl)methyl]cyclohexan-1-ol Chemical compound C=1C=C(Cl)C=CC=1CC1(O)CCCCC1 RHDLCEUYNPSLDK-UHFFFAOYSA-N 0.000 description 1
- MDZJRWIPTIVZKF-UHFFFAOYSA-N 1-[(4-methylphenyl)methyl]cyclohexan-1-ol Chemical compound C1=CC(C)=CC=C1CC1(O)CCCCC1 MDZJRWIPTIVZKF-UHFFFAOYSA-N 0.000 description 1
- RTRTUCOUELDWEX-UHFFFAOYSA-N 1-benzylcycloheptan-1-ol Chemical compound C=1C=CC=CC=1CC1(O)CCCCCC1 RTRTUCOUELDWEX-UHFFFAOYSA-N 0.000 description 1
- FELACZRZMOTSPB-UHFFFAOYSA-N 1-benzylcyclohexan-1-ol Chemical compound C=1C=CC=CC=1CC1(O)CCCCC1 FELACZRZMOTSPB-UHFFFAOYSA-N 0.000 description 1
- MGIVULDROKOUIN-UHFFFAOYSA-N 1-benzylcyclooctan-1-ol Chemical compound C=1C=CC=CC=1CC1(O)CCCCCCC1 MGIVULDROKOUIN-UHFFFAOYSA-N 0.000 description 1
- ZNZISHNDYHTHKL-UHFFFAOYSA-N 1-benzylcyclopentan-1-ol Chemical compound C=1C=CC=CC=1CC1(O)CCCC1 ZNZISHNDYHTHKL-UHFFFAOYSA-N 0.000 description 1
- 125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 101150106671 COMT gene Proteins 0.000 description 1
- 241000700199 Cavia porcellus Species 0.000 description 1
- 238000003747 Grignard reaction Methods 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 208000006550 Mydriasis Diseases 0.000 description 1
- LNEMISWPJLTREW-UHFFFAOYSA-N OC1(CC2=CC=C(Cl)C=C2)CCCCCCC1 Chemical compound OC1(CC2=CC=C(Cl)C=C2)CCCCCCC1 LNEMISWPJLTREW-UHFFFAOYSA-N 0.000 description 1
- 208000027089 Parkinsonian disease Diseases 0.000 description 1
- 206010044565 Tremor Diseases 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000001004 anti-acetylcholinic effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 125000005853 β-dimethylaminoethyl group Chemical group 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Hydrogenated Pyridines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB54661A DE1094738B (de) | 1959-09-03 | 1959-09-03 | Verfahren zur Herstellung neuer, auf das Zentralnervensystem hemmend wirkender basischer AEther, deren Salzen und quaternaeren Ammoniumverbindungen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH388939A true CH388939A (de) | 1965-03-15 |
Family
ID=6970693
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH862060A CH388939A (de) | 1959-09-03 | 1960-07-28 | Verfahren zur Herstellung neuer, auf das Zentralnervensystem hemmend wirkender, basischer Äther |
Country Status (4)
| Country | Link |
|---|---|
| BE (1) | BE594572A (en(2012)) |
| CH (1) | CH388939A (en(2012)) |
| DE (1) | DE1094738B (en(2012)) |
| LU (1) | LU38979A1 (en(2012)) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0014017A1 (en) * | 1979-01-26 | 1980-08-06 | Chem. Pharmaz. Fabrik Dr. Hermann Thiemann GmbH | 1-(Omega-aminoalkoxy)-3,3,5-trimethylcyclohexanes, processes for their preparation and pharmaceutical compositions containing same |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1090201B (de) * | 1959-05-02 | 1960-10-06 | Boehringer & Soehne Gmbh | Verfahren zur Herstellung neuer basischer therapeutisch wirksamer AEther bzw. deren Salzen |
| DE1792788A1 (de) * | 1966-01-15 | 1976-10-21 | Egyt Gyogyszervegyeszeti Gyar | Peripher vasodilatorisch wirksames arzneimittel |
-
1959
- 1959-09-03 DE DEB54661A patent/DE1094738B/de active Pending
-
1960
- 1960-07-21 LU LU38979D patent/LU38979A1/xx unknown
- 1960-07-28 CH CH862060A patent/CH388939A/de unknown
- 1960-08-30 BE BE594572A patent/BE594572A/fr unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0014017A1 (en) * | 1979-01-26 | 1980-08-06 | Chem. Pharmaz. Fabrik Dr. Hermann Thiemann GmbH | 1-(Omega-aminoalkoxy)-3,3,5-trimethylcyclohexanes, processes for their preparation and pharmaceutical compositions containing same |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1094738B (de) | 1960-12-15 |
| LU38979A1 (en(2012)) | 1960-10-21 |
| BE594572A (fr) | 1961-02-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| WO1985002847A1 (fr) | Esters et amides d'acides carboniques carbocycliques et heterocycliques d'amines ou d'alcools azotes cycliques portes et non portes | |
| DE1220440B (de) | Verfahren zur Herstellung von Derivaten des 1-(o-Bromphenoxy)-2-hydroxy-3-amino-propans und deren Saeureadditionssalzen | |
| CH388939A (de) | Verfahren zur Herstellung neuer, auf das Zentralnervensystem hemmend wirkender, basischer Äther | |
| DE1807218A1 (de) | Oxotremorin-Antagonisten und Verfahren zu deren Herstellung | |
| CH419105A (de) | Verfahren zur Herstellung analeptisch wirksamer N-substituierter Amino-norcamphanderivate bzw. von deren Säureadditionssalzen und quaternären Ammoniumverbindungen | |
| AT219586B (de) | Verfahren zur Herstellung neuer basischer Äther und deren Salze | |
| AT217024B (de) | Verfahren zur Herstellung neuer basischer Äther, sowie ihrer Salze und quartären Ammoniumverbindungen | |
| DE1088481B (de) | Verfahren zur Herstellung neuer Verbindungen der Tetracyclinreihe | |
| AT219561B (de) | Verfahren zur Herstellung neuer basischer Äther und ihrer salzartigen Abkömmlinge | |
| DE2822473C2 (de) | Alkanolaminderivate und pharmazeutische Mittel, welche diese Alkanolaminderivate enthalten | |
| EP0117531A1 (de) | N-(3-Trifluormethylphenyl)-N'-propargylpiperazin, seine Herstellung und Verwendung | |
| DE1005067B (de) | Verfahren zur Herstellung von bicyclisch substituierten Aminopropanolen | |
| DE1090201B (de) | Verfahren zur Herstellung neuer basischer therapeutisch wirksamer AEther bzw. deren Salzen | |
| CH356121A (de) | Verfahren zur Herstellung von N-monosubstituierten Amiden vona-Aminoalkyl-a-phenyl-essigsäuren | |
| DE1110155B (de) | Verfahren zur Herstellung neuer basischer AEther bzw. deren Salzen mit Antiparkinsonwirkung | |
| AT226691B (de) | Verfahren zur Herstellung von neuen 2,5-disubstituierten Pyrrolidinen | |
| DE623593C (en(2012)) | ||
| DE936268C (de) | Verfahren zur Herstellung von neuen N-Methyl-trimethyl-colchicinsaeureamiden und ihren Salzen | |
| AT220619B (de) | Verfahren zur Herstellung von Aminoalkylbenzhydryläthern | |
| AT284088B (de) | Verfahren zur Herstellung von neuen, 1-Phenoxy-2-aminoalkanen und von deren Säureadditionssalzen | |
| DE1618160C3 (de) | l-(2-Äthinylphenoxy)-2-hydroxy-3alkylaminopropane, ihre physiologisch verträglichen Säureadditionssalze, Verfahren zu ihrer Herstellung, sowie diese Verbindungen enthaltende Arzneimittel | |
| AT214933B (de) | Verfahren zur Herstellung von neuen 3-substituierten 1-Alkylazetidinen | |
| AT237603B (de) | Verfahren zur Herstellung von neuen o-Toluididen | |
| AT273929B (de) | Verfahren zur Herstellung von neuen 1-(2'-Methyl- oder -Methoxy-3',4'-dihydroxyphenyl)-2-isopropylaminoalkanolen | |
| DE1166787B (de) | Verfahren zur Herstellung von neuen Granatanol-(3ª‰)-estern und ihren Hydrohalogeniden |