NO133273B - - Google Patents
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- Publication number
- NO133273B NO133273B NO2928/71A NO292871A NO133273B NO 133273 B NO133273 B NO 133273B NO 2928/71 A NO2928/71 A NO 2928/71A NO 292871 A NO292871 A NO 292871A NO 133273 B NO133273 B NO 133273B
- Authority
- NO
- Norway
- Prior art keywords
- methyl
- formula
- phenylbenzyl
- piperidine
- denotes
- Prior art date
Links
- -1 methyl compound Chemical class 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- 150000001450 anions Chemical class 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- NNCAWEWCFVZOGF-UHFFFAOYSA-N mepiquat Chemical group C[N+]1(C)CCCCC1 NNCAWEWCFVZOGF-UHFFFAOYSA-N 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 32
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 6
- 239000008096 xylene Substances 0.000 description 6
- 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 description 5
- 239000002253 acid Substances 0.000 description 5
- 230000001078 anti-cholinergic effect Effects 0.000 description 5
- 230000001387 anti-histamine Effects 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- 239000000739 antihistaminic agent Substances 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- 150000003512 tertiary amines Chemical class 0.000 description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001340 alkali metals Chemical group 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000005956 quaternization reaction Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- HXXJMMLIEYAFOZ-UHFFFAOYSA-N (1-methylpiperidin-2-yl)methanol Chemical compound CN1CCCCC1CO HXXJMMLIEYAFOZ-UHFFFAOYSA-N 0.000 description 2
- YDZWTSSVMMUNIS-UHFFFAOYSA-N (1-methylpiperidin-2-yl)methanol;hydrochloride Chemical compound Cl.CN1CCCCC1CO YDZWTSSVMMUNIS-UHFFFAOYSA-N 0.000 description 2
- GAUKKFMRLMOULV-UHFFFAOYSA-N 1-iodopiperidine Chemical compound IN1CCCCC1 GAUKKFMRLMOULV-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000005557 antagonist Substances 0.000 description 2
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- RRNSKPOVJIKVNB-UHFFFAOYSA-N 1-[chloro(phenyl)methyl]-4-methylbenzene Chemical compound C1=CC(C)=CC=C1C(Cl)C1=CC=CC=C1 RRNSKPOVJIKVNB-UHFFFAOYSA-N 0.000 description 1
- RRQGZMDHLIAOLY-UHFFFAOYSA-N 1-bromopiperidine Chemical compound BrN1CCCCC1 RRQGZMDHLIAOLY-UHFFFAOYSA-N 0.000 description 1
- FWWOWPGPERBCNJ-UHFFFAOYSA-N 2-hydroxy-4-(2-hydroxyethoxy)-4-oxobutanoic acid Chemical compound OCCOC(=O)CC(O)C(O)=O FWWOWPGPERBCNJ-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 208000006550 Mydriasis Diseases 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 1
- 150000008046 alkali metal hydrides Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 229940065524 anticholinergics inhalants for obstructive airway diseases Drugs 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000812 cholinergic antagonist Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- QILSFLSDHQAZET-UHFFFAOYSA-N diphenylmethanol Chemical compound C=1C=CC=CC=1C(O)C1=CC=CC=C1 QILSFLSDHQAZET-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- HEDXEAAVEOJUCR-UHFFFAOYSA-N furtrethonium Chemical compound C[N+](C)(C)CC1=CC=CO1 HEDXEAAVEOJUCR-UHFFFAOYSA-N 0.000 description 1
- 229950008234 furtrethonium Drugs 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229960004931 histamine dihydrochloride Drugs 0.000 description 1
- PPZMYIBUHIPZOS-UHFFFAOYSA-N histamine dihydrochloride Chemical compound Cl.Cl.NCCC1=CN=CN1 PPZMYIBUHIPZOS-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 210000003405 ileum Anatomy 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 210000001630 jejunum Anatomy 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 229940102396 methyl bromide Drugs 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 210000000813 small intestine Anatomy 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C07D211/20—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 singly bound oxygen or sulphur atoms
- C07D211/22—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 singly bound oxygen or sulphur atoms by oxygen atoms
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 |
---|---|---|---|
GB37746/70A GB1299289A (en) | 1970-08-05 | 1970-08-05 | Piperidine derivatives |
Publications (2)
Publication Number | Publication Date |
---|---|
NO133273B true NO133273B (xx) | 1975-12-29 |
NO133273C NO133273C (xx) | 1976-04-07 |
Family
ID=10398735
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO2928/71A NO133273C (xx) | 1970-08-05 | 1971-08-04 |
Country Status (18)
Country | Link |
---|---|
US (1) | US4228287A (xx) |
AT (1) | AT308114B (xx) |
AU (1) | AU450147B2 (xx) |
BE (1) | BE770959A (xx) |
CA (1) | CA955939A (xx) |
CH (1) | CH554862A (xx) |
DE (1) | DE2139099C3 (xx) |
DK (1) | DK125999B (xx) |
ES (1) | ES393894A1 (xx) |
FI (1) | FI52215C (xx) |
FR (1) | FR2101245B1 (xx) |
GB (1) | GB1299289A (xx) |
IL (1) | IL37438A (xx) |
LU (1) | LU63665A1 (xx) |
NL (1) | NL7110728A (xx) |
NO (1) | NO133273C (xx) |
SE (1) | SE369899B (xx) |
ZA (1) | ZA715156B (xx) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5703088A (en) * | 1989-08-21 | 1997-12-30 | Beth Israel Deaconess Medical Center, Inc. | Topical application of spiperone or derivatives thereof for treatment of pathological conditions associated with immune responses |
US5574041A (en) * | 1990-03-16 | 1996-11-12 | Beth Israel Hospital Association | Use of spiperone derivatives as immunosuppressant agents |
US5693645A (en) * | 1992-12-23 | 1997-12-02 | Beth Israel Deaconess Medical Center, Inc. | Use of spiperone or spiperone derivatives as immunosuppressant agents |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3097212A (en) * | 1963-07-09 | N-methyl-z- | ||
US2508422A (en) * | 1946-01-11 | 1950-05-23 | Parke Davis & Co | Quaternary ammonium halides of amino benzhydryl ethers |
US2567351A (en) * | 1946-01-29 | 1951-09-11 | Parke Davis & Co | Process for the manufacture of benzhydryl ethers |
US2751388A (en) * | 1950-04-07 | 1956-06-19 | Nopco Chem Co | Process for preparing benzhydryl ethers |
US2708194A (en) * | 1952-12-10 | 1955-05-10 | Univ Michigan | 2-(1-methyl) polymethyleniminylmethyl benzhydryl ethers and preparation thereof |
-
1970
- 1970-08-05 GB GB37746/70A patent/GB1299289A/en not_active Expired
-
1971
- 1971-07-27 US US05/166,641 patent/US4228287A/en not_active Expired - Lifetime
- 1971-08-03 ZA ZA715156A patent/ZA715156B/xx unknown
- 1971-08-04 DE DE2139099A patent/DE2139099C3/de not_active Expired
- 1971-08-04 CA CA119,779A patent/CA955939A/en not_active Expired
- 1971-08-04 LU LU63665D patent/LU63665A1/xx unknown
- 1971-08-04 DK DK381071AA patent/DK125999B/da not_active IP Right Cessation
- 1971-08-04 BE BE770959A patent/BE770959A/xx unknown
- 1971-08-04 AU AU31979/71A patent/AU450147B2/en not_active Expired
- 1971-08-04 AT AT680771A patent/AT308114B/de not_active IP Right Cessation
- 1971-08-04 ES ES393894A patent/ES393894A1/es not_active Expired
- 1971-08-04 IL IL37438A patent/IL37438A/en unknown
- 1971-08-04 CH CH1148371A patent/CH554862A/xx not_active IP Right Cessation
- 1971-08-04 NO NO2928/71A patent/NO133273C/no unknown
- 1971-08-04 FI FI712195A patent/FI52215C/fi active
- 1971-08-04 SE SE09980/71A patent/SE369899B/xx unknown
- 1971-08-04 FR FR7128611A patent/FR2101245B1/fr not_active Expired
- 1971-08-04 NL NL7110728A patent/NL7110728A/xx not_active Application Discontinuation
Also Published As
Publication number | Publication date |
---|---|
AU3197971A (en) | 1973-02-08 |
CH554862A (de) | 1974-10-15 |
DE2139099B2 (de) | 1980-06-12 |
AT308114B (de) | 1973-06-25 |
LU63665A1 (xx) | 1971-12-13 |
SE369899B (xx) | 1974-09-23 |
BE770959A (fr) | 1972-02-04 |
FR2101245B1 (xx) | 1974-09-06 |
AU450147B2 (en) | 1974-06-27 |
NO133273C (xx) | 1976-04-07 |
FI52215B (xx) | 1977-03-31 |
DE2139099A1 (de) | 1972-02-10 |
NL7110728A (xx) | 1972-02-08 |
IL37438A0 (en) | 1971-11-29 |
FR2101245A1 (xx) | 1972-03-31 |
US4228287A (en) | 1980-10-14 |
IL37438A (en) | 1974-11-29 |
ES393894A1 (es) | 1973-09-16 |
FI52215C (fi) | 1977-07-11 |
DK125999B (da) | 1973-05-28 |
CA955939A (en) | 1974-10-08 |
GB1299289A (en) | 1972-12-13 |
ZA715156B (en) | 1972-04-26 |
DE2139099C3 (de) | 1981-02-26 |
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