IE42065B1 - Cyproheptadine derivatives - Google Patents
Cyproheptadine derivativesInfo
- Publication number
- IE42065B1 IE42065B1 IE2510/75A IE251075A IE42065B1 IE 42065 B1 IE42065 B1 IE 42065B1 IE 2510/75 A IE2510/75 A IE 2510/75A IE 251075 A IE251075 A IE 251075A IE 42065 B1 IE42065 B1 IE 42065B1
- Authority
- IE
- Ireland
- Prior art keywords
- oxide
- composition
- dibenzo
- cyproheptadine
- isomer
- Prior art date
Links
- JJCFRYNCJDLXIK-UHFFFAOYSA-N cyproheptadine Chemical class C1CN(C)CCC1=C1C2=CC=CC=C2C=CC2=CC=CC=C21 JJCFRYNCJDLXIK-UHFFFAOYSA-N 0.000 title description 2
- 239000000203 mixture Substances 0.000 claims abstract description 10
- 150000003839 salts Chemical class 0.000 claims abstract description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 6
- 241001465754 Metazoa Species 0.000 claims description 4
- 239000002552 dosage form Substances 0.000 claims description 4
- 238000005377 adsorption chromatography Methods 0.000 claims description 2
- 239000007900 aqueous suspension Substances 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims 1
- 229940102223 injectable solution Drugs 0.000 claims 1
- 230000036528 appetite Effects 0.000 abstract 1
- 235000019789 appetite Nutrition 0.000 abstract 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 abstract 1
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- 239000000546 pharmaceutical excipient Substances 0.000 abstract 1
- 238000000926 separation method Methods 0.000 abstract 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
- 239000000377 silicon dioxide Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- AIAORTASLOWFGX-UHFFFAOYSA-N 4-(dibenzo[1,2-a:1',2'-e][7]annulen-11-ylidene)-1-methyl-1-oxidopiperidin-1-ium Chemical compound C1C[N+](C)([O-])CCC1=C1C2=CC=CC=C2C=CC2=CC=CC=C21 AIAORTASLOWFGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 229920002472 Starch Polymers 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 239000001506 calcium phosphate Substances 0.000 description 3
- 229910000389 calcium phosphate Inorganic materials 0.000 description 3
- 235000011010 calcium phosphates Nutrition 0.000 description 3
- 229960001140 cyproheptadine Drugs 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 239000008101 lactose Substances 0.000 description 3
- 235000019359 magnesium stearate Nutrition 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000008107 starch Substances 0.000 description 3
- 235000019698 starch Nutrition 0.000 description 3
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 3
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 230000007943 positive regulation of appetite Effects 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000007916 tablet composition Substances 0.000 description 2
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
- 208000004998 Abdominal Pain Diseases 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- 208000002881 Colic Diseases 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000003651 drinking water Substances 0.000 description 1
- 235000020188 drinking water Nutrition 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- QMEZUZOCLYUADC-UHFFFAOYSA-N hydrate;dihydrochloride Chemical compound O.Cl.Cl QMEZUZOCLYUADC-UHFFFAOYSA-N 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 235000014571 nuts Nutrition 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 238000005303 weighing Methods 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
- C07D211/92—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with a hetero atom directly attached to the ring nitrogen atom
- C07D211/94—Oxygen atom, e.g. piperidine N-oxide
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/525,324 US3992547A (en) | 1974-11-20 | 1974-11-20 | 4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-methylpiperidine-N-oxide isomer |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE42065L IE42065L (en) | 1976-05-20 |
| IE42065B1 true IE42065B1 (en) | 1980-05-21 |
Family
ID=24092770
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE2510/75A IE42065B1 (en) | 1974-11-20 | 1975-11-18 | Cyproheptadine derivatives |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US3992547A (enExample) |
| JP (1) | JPS5175077A (enExample) |
| AR (1) | AR208726A1 (enExample) |
| BE (1) | BE835723A (enExample) |
| CA (1) | CA1060001A (enExample) |
| DE (1) | DE2551976A1 (enExample) |
| DK (1) | DK496875A (enExample) |
| FR (1) | FR2291752A1 (enExample) |
| GB (1) | GB1478285A (enExample) |
| IE (1) | IE42065B1 (enExample) |
| LU (1) | LU73822A1 (enExample) |
| NL (1) | NL7512867A (enExample) |
| OA (1) | OA05166A (enExample) |
| PH (1) | PH12081A (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005232002A (ja) * | 2001-04-02 | 2005-09-02 | Ajinomoto Co Inc | デスメチルサイプロヘプタジンの製造方法および精製方法 |
| CN104133012B (zh) * | 2014-07-02 | 2020-01-07 | 北京万全德众医药生物技术有限公司 | 一种高效液相色谱法测定马来酸阿塞那平消旋体的方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3014911A (en) * | 1958-09-29 | 1961-12-26 | Merck & Co Inc | Derivatives of dibenzo[a, e]cycloheptatriene |
| US3642808A (en) * | 1964-05-06 | 1972-02-15 | Ciba Geigy Corp | (dibenzo(a d)-cycloheptene-5'-ylidene)-1-hydroxy piperidine |
| US3851059A (en) * | 1970-02-05 | 1974-11-26 | Merck & Co Inc | Method for the stimulation of appetite in patients |
-
1974
- 1974-11-20 US US05/525,324 patent/US3992547A/en not_active Expired - Lifetime
-
1975
- 1975-11-03 NL NL7512867A patent/NL7512867A/xx not_active Application Discontinuation
- 1975-11-05 DK DK496875A patent/DK496875A/da unknown
- 1975-11-10 CA CA239,599A patent/CA1060001A/en not_active Expired
- 1975-11-12 AR AR261149A patent/AR208726A1/es active
- 1975-11-12 PH PH17762A patent/PH12081A/en unknown
- 1975-11-18 IE IE2510/75A patent/IE42065B1/en unknown
- 1975-11-18 FR FR7535151A patent/FR2291752A1/fr active Granted
- 1975-11-18 LU LU73822A patent/LU73822A1/xx unknown
- 1975-11-18 OA OA55667A patent/OA05166A/xx unknown
- 1975-11-18 GB GB4748775A patent/GB1478285A/en not_active Expired
- 1975-11-19 BE BE161998A patent/BE835723A/xx unknown
- 1975-11-19 DE DE19752551976 patent/DE2551976A1/de not_active Withdrawn
- 1975-11-20 JP JP50138819A patent/JPS5175077A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| AU8649175A (en) | 1977-05-19 |
| GB1478285A (en) | 1977-06-29 |
| DE2551976A1 (de) | 1976-05-26 |
| FR2291752B1 (enExample) | 1980-06-20 |
| PH12081A (en) | 1978-10-30 |
| JPS5175077A (en) | 1976-06-29 |
| LU73822A1 (enExample) | 1976-09-06 |
| AR208726A1 (es) | 1977-02-28 |
| OA05166A (fr) | 1981-01-31 |
| FR2291752A1 (fr) | 1976-06-18 |
| DK496875A (da) | 1976-05-21 |
| IE42065L (en) | 1976-05-20 |
| CA1060001A (en) | 1979-08-07 |
| BE835723A (fr) | 1976-05-19 |
| US3992547A (en) | 1976-11-16 |
| NL7512867A (nl) | 1976-05-24 |
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