US3627775A - 1-alkyl-1,2,5,6-tetrahydro-3-pyridylmethyl carboxylic - Google Patents
1-alkyl-1,2,5,6-tetrahydro-3-pyridylmethyl carboxylic Download PDFInfo
- Publication number
- US3627775A US3627775A US836658A US3627775DA US3627775A US 3627775 A US3627775 A US 3627775A US 836658 A US836658 A US 836658A US 3627775D A US3627775D A US 3627775DA US 3627775 A US3627775 A US 3627775A
- Authority
- US
- United States
- Prior art keywords
- tetrahydro
- pyridylmethyl
- carbon atoms
- alkyl
- acid ester
- Prior art date
- 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 - Lifetime
Links
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 28
- 150000001875 compounds Chemical class 0.000 claims abstract description 28
- 239000002253 acid Substances 0.000 claims abstract description 25
- 150000003839 salts Chemical class 0.000 claims abstract description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 14
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 12
- 231100000252 nontoxic Toxicity 0.000 claims abstract description 11
- 230000003000 nontoxic effect Effects 0.000 claims abstract description 11
- 239000001257 hydrogen Substances 0.000 claims abstract description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 10
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims abstract description 9
- 229940087675 benzilic acid Drugs 0.000 claims description 36
- -1 1-n-hexyl-1,2,5, 6-tetrahydro-3-pyridylmethyl benzilic acid ester Chemical class 0.000 claims description 25
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 5
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 5
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
- 125000000094 2-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 2
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract description 12
- 230000002048 spasmolytic effect Effects 0.000 abstract description 9
- 125000000753 cycloalkyl group Chemical group 0.000 abstract description 7
- 230000000694 effects Effects 0.000 abstract description 6
- 150000001733 carboxylic acid esters Chemical class 0.000 abstract description 5
- 239000000812 cholinergic antagonist Substances 0.000 abstract description 5
- 229910052799 carbon Inorganic materials 0.000 abstract description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract description 4
- 125000003342 alkenyl group Chemical group 0.000 abstract description 3
- 125000003545 alkoxy group Chemical group 0.000 abstract description 3
- 125000004430 oxygen atom Chemical group O* 0.000 abstract description 3
- 125000003884 phenylalkyl group Chemical group 0.000 abstract description 3
- 230000001624 sedative effect Effects 0.000 abstract description 3
- 125000000304 alkynyl group Chemical group 0.000 abstract description 2
- 125000004093 cyano group Chemical group *C#N 0.000 abstract description 2
- 229910052736 halogen Inorganic materials 0.000 abstract description 2
- 150000002367 halogens Chemical class 0.000 abstract description 2
- 150000002431 hydrogen Chemical group 0.000 abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 30
- 238000000034 method Methods 0.000 description 29
- 238000002844 melting Methods 0.000 description 28
- 230000008018 melting Effects 0.000 description 28
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- 238000007792 addition Methods 0.000 description 11
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
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- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
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- 208000007101 Muscle Cramp Diseases 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 208000005392 Spasm Diseases 0.000 description 2
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- 208000001871 Tachycardia Diseases 0.000 description 2
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- 230000029936 alkylation Effects 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- YTRNSQPXEDGWMR-UHFFFAOYSA-N alpha-Cyclohexylmandelic acid Chemical compound C=1C=CC=CC=1C(O)(C(=O)O)C1CCCCC1 YTRNSQPXEDGWMR-UHFFFAOYSA-N 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
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- 125000005843 halogen group Chemical group 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 229940098779 methanesulfonic acid Drugs 0.000 description 2
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- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 2
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- XETLOFNELZCXMX-UHFFFAOYSA-N 2-(diethylamino)ethyl 2-(4-hexoxyphenyl)-2-hydroxy-2-phenylacetate;hydrochloride Chemical compound Cl.C1=CC(OCCCCCC)=CC=C1C(O)(C(=O)OCCN(CC)CC)C1=CC=CC=C1 XETLOFNELZCXMX-UHFFFAOYSA-N 0.000 description 1
- FYELSNVLZVIGTI-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-5-ethylpyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C=1C=NN(C=1CC)CC(=O)N1CC2=C(CC1)NN=N2 FYELSNVLZVIGTI-UHFFFAOYSA-N 0.000 description 1
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- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
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- 244000215068 Acacia senegal Species 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
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- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
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- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
-
- 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
Definitions
- R is phenyl, cyclopentyl or cyclohexyl
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT609868A AT287711B (de) | 1968-06-25 | 1968-06-25 | Verfahren zur Herstellung von neuen 1-Alkyl-1,2,5,6-tetrahydro-3-pyridylmethyl-carbonsäureestern sowie deren Säureadditionssalzen und quaternären Ammoniumverbindungen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3627775A true US3627775A (en) | 1971-12-14 |
Family
ID=3582843
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US836658A Expired - Lifetime US3627775A (en) | 1968-06-25 | 1969-06-25 | 1-alkyl-1,2,5,6-tetrahydro-3-pyridylmethyl carboxylic |
Country Status (11)
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4467095A (en) * | 1969-02-10 | 1984-08-21 | Fmc Corporation | Anticholinergic compounds |
| US4472408A (en) * | 1981-03-11 | 1984-09-18 | Sanofi | Substituted trifluoromethylphenyltetrahydropyridines having an anorectic activity |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3879556A (en) * | 1970-09-02 | 1975-04-22 | Boehringer Sohn Ingelheim | Pharmaceutical compositions containing a 1,2,3,6-tetrahydro-4-pyridylmethyl carboxylate and method of use |
| DE2043455A1 (de) * | 1970-09-02 | 1972-03-09 | CH. Boehringer Sohn, 6507 Ingelheim | Neue l,2,3,6-tetrahydro-4-pyridylmethyl-carbonsäureester, sowie deren Säureadditionssalze und quarternären Ammoniumverbindungen |
| DE3801659A1 (de) * | 1988-01-21 | 1989-07-27 | Boehringer Ingelheim Kg | Tetrahydropyridin - derivate |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2607777A (en) * | 1947-04-10 | 1952-08-19 | Searle & Co | N-alkyl piperidyl alkyl esters of diphenyl acetic acid and 9-fluorenyl carboxylic acid |
| GB886437A (en) * | 1959-07-15 | 1962-01-10 | Beecham Res Lab | Improvements in or relating to basic esters of etherified benzilic acids |
-
1968
- 1968-06-25 AT AT609868A patent/AT287711B/de not_active IP Right Cessation
-
1969
- 1969-06-12 DE DE19691929921 patent/DE1929921A1/de active Pending
- 1969-06-19 NL NL6909425A patent/NL6909425A/xx unknown
- 1969-06-23 CH CH958769A patent/CH513164A/de not_active IP Right Cessation
- 1969-06-23 ES ES368698A patent/ES368698A1/es not_active Expired
- 1969-06-24 IL IL32469A patent/IL32469A0/xx unknown
- 1969-06-24 BR BR210094/69A patent/BR6910094D0/pt unknown
- 1969-06-25 FR FR6921376A patent/FR2014218A1/fr not_active Withdrawn
- 1969-06-25 BE BE735141D patent/BE735141A/xx unknown
- 1969-06-25 GB GB1257960D patent/GB1257960A/en not_active Expired
- 1969-06-25 US US836658A patent/US3627775A/en not_active Expired - Lifetime
- 1969-12-10 ES ES374408A patent/ES374408A1/es not_active Expired
- 1969-12-10 ES ES374407A patent/ES374407A1/es not_active Expired
Non-Patent Citations (2)
| Title |
|---|
| Benington et al., J. Org. Chem., Vol. 25, No. 11, pp. 1,912 1,916, 1960 QD241J.6 * |
| Burger, Medicinal Chemistry, Second Edition, Interscience, pp. 497, 1960 RS 403 B 8 1960 C.7 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4467095A (en) * | 1969-02-10 | 1984-08-21 | Fmc Corporation | Anticholinergic compounds |
| US4472408A (en) * | 1981-03-11 | 1984-09-18 | Sanofi | Substituted trifluoromethylphenyltetrahydropyridines having an anorectic activity |
| US4602024A (en) * | 1981-03-11 | 1986-07-22 | Sanofi | Substituted trifluoromethylphenyltetrahydropyridines having a cyano substituent and an anorectic activity, a process for preparing same and pharmaceutical compositions |
Also Published As
| Publication number | Publication date |
|---|---|
| ES374408A1 (es) | 1972-01-01 |
| GB1257960A (enrdf_load_stackoverflow) | 1971-12-22 |
| BE735141A (enrdf_load_stackoverflow) | 1969-12-29 |
| ES374407A1 (es) | 1972-01-01 |
| DE1929921A1 (de) | 1970-01-02 |
| BR6910094D0 (pt) | 1973-04-05 |
| IL32469A0 (en) | 1969-08-27 |
| FR2014218A1 (enrdf_load_stackoverflow) | 1970-04-17 |
| NL6909425A (enrdf_load_stackoverflow) | 1969-12-30 |
| CH513164A (de) | 1971-09-30 |
| AT287711B (de) | 1971-02-10 |
| ES368698A1 (es) | 1971-07-01 |
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