GB853775A - Pharmaceutical compositions and methods for producing phenylcyclohexane compounds - Google Patents
Pharmaceutical compositions and methods for producing phenylcyclohexane compoundsInfo
- Publication number
- GB853775A GB853775A GB6414/58A GB641458A GB853775A GB 853775 A GB853775 A GB 853775A GB 6414/58 A GB6414/58 A GB 6414/58A GB 641458 A GB641458 A GB 641458A GB 853775 A GB853775 A GB 853775A
- Authority
- GB
- United Kingdom
- Prior art keywords
- phenyl
- acid
- prepared
- reacting
- cyclohexanone
- 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
Links
- 238000000034 method Methods 0.000 title abstract 2
- 239000008194 pharmaceutical composition Substances 0.000 title abstract 2
- IGARGHRYKHJQSM-UHFFFAOYSA-N cyclohexylbenzene Chemical class C1CCCCC1C1=CC=CC=C1 IGARGHRYKHJQSM-UHFFFAOYSA-N 0.000 title 1
- -1 alkyl 1-phenylcyclohexane carboxylate Chemical compound 0.000 abstract 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 6
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Substances CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 5
- 239000002253 acid Substances 0.000 abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 abstract 4
- 238000010992 reflux Methods 0.000 abstract 4
- 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 abstract 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 abstract 3
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract 3
- 239000007788 liquid Substances 0.000 abstract 3
- 239000011707 mineral Substances 0.000 abstract 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 3
- RKNUEXASLVLVSL-UHFFFAOYSA-N 1-phenylcyclohexane-1-carboxamide Chemical compound C=1C=CC=CC=1C1(C(=O)N)CCCCC1 RKNUEXASLVLVSL-UHFFFAOYSA-N 0.000 abstract 2
- RGZGRPPQZUQUCR-UHFFFAOYSA-N 1-phenylcyclohexylamine Chemical compound C=1C=CC=CC=1C1(N)CCCCC1 RGZGRPPQZUQUCR-UHFFFAOYSA-N 0.000 abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 abstract 2
- 239000003513 alkali Substances 0.000 abstract 2
- 229910052783 alkali metal Inorganic materials 0.000 abstract 2
- 150000001340 alkali metals Chemical class 0.000 abstract 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 abstract 2
- 239000002775 capsule Substances 0.000 abstract 2
- 239000012280 lithium aluminium hydride Substances 0.000 abstract 2
- 229910052749 magnesium Inorganic materials 0.000 abstract 2
- 239000011777 magnesium Substances 0.000 abstract 2
- QXDFOWJXUCIHGJ-UHFFFAOYSA-N n-benzyl-1-phenylcyclohexan-1-amine Chemical compound C=1C=CC=CC=1CNC1(C=2C=CC=CC=2)CCCCC1 QXDFOWJXUCIHGJ-UHFFFAOYSA-N 0.000 abstract 2
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 239000000829 suppository Substances 0.000 abstract 2
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 abstract 1
- JRSWMPZCZFGIFD-UHFFFAOYSA-N (1-isothiocyanatocyclohexyl)benzene Chemical compound C=1C=CC=CC=1C1(N=C=S)CCCCC1 JRSWMPZCZFGIFD-UHFFFAOYSA-N 0.000 abstract 1
- RATMDIXKNCIQOD-UHFFFAOYSA-N (1-methylcyclohexyl)benzene Chemical compound C=1C=CC=CC=1C1(C)CCCCC1 RATMDIXKNCIQOD-UHFFFAOYSA-N 0.000 abstract 1
- ZYFIHZPPXQYKSM-UHFFFAOYSA-N (1-phenylcyclohexyl)hydrazine Chemical compound C1(=CC=CC=C1)C1(CCCCC1)NN ZYFIHZPPXQYKSM-UHFFFAOYSA-N 0.000 abstract 1
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 abstract 1
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 abstract 1
- KXSMAXBVGMBNET-UHFFFAOYSA-N 1-methyl-1-phenyl-2-(1-phenylcyclohexyl)hydrazine Chemical compound C1(=CC=CC=C1)N(NC1(CCCCC1)C1=CC=CC=C1)C KXSMAXBVGMBNET-UHFFFAOYSA-N 0.000 abstract 1
- MWOODERJGVWYJE-UHFFFAOYSA-N 1-methyl-1-phenylhydrazine Chemical compound CN(N)C1=CC=CC=C1 MWOODERJGVWYJE-UHFFFAOYSA-N 0.000 abstract 1
- QXXHHHWXFHPNOS-UHFFFAOYSA-N 1-phenylcyclohexane-1-carboxylic acid Chemical compound C=1C=CC=CC=1C1(C(=O)O)CCCCC1 QXXHHHWXFHPNOS-UHFFFAOYSA-N 0.000 abstract 1
- IXDGGSSUYSFGOK-UHFFFAOYSA-N 2-amino-2-phenylcyclohexan-1-one Chemical compound C=1C=CC=CC=1C1(N)CCCCC1=O IXDGGSSUYSFGOK-UHFFFAOYSA-N 0.000 abstract 1
- LXSSSYHJHAVQCI-UHFFFAOYSA-N 2-nitroso-2-phenylcyclohexan-1-one Chemical compound C1(=CC=CC=C1)C1(C(CCCC1)=O)N=O LXSSSYHJHAVQCI-UHFFFAOYSA-N 0.000 abstract 1
- DRLVMOAWNVOSPE-UHFFFAOYSA-N 2-phenylcyclohexan-1-one Chemical compound O=C1CCCCC1C1=CC=CC=C1 DRLVMOAWNVOSPE-UHFFFAOYSA-N 0.000 abstract 1
- WCMSFBRREKZZFL-UHFFFAOYSA-N 3-cyclohexen-1-yl-Benzene Chemical compound C1CCCC(C=2C=CC=CC=2)=C1 WCMSFBRREKZZFL-UHFFFAOYSA-N 0.000 abstract 1
- VMPHJJHZNSQKLI-UHFFFAOYSA-N 4-amino-4-phenylcyclohexan-1-ol Chemical compound C=1C=CC=CC=1C1(N)CCC(O)CC1 VMPHJJHZNSQKLI-UHFFFAOYSA-N 0.000 abstract 1
- JXNHEUAANNGFFV-UHFFFAOYSA-N 4-amino-4-phenylcyclohexan-1-one Chemical compound C=1C=CC=CC=1C1(N)CCC(=O)CC1 JXNHEUAANNGFFV-UHFFFAOYSA-N 0.000 abstract 1
- QNKKWFGKBDIZCJ-UHFFFAOYSA-N 5-amino-2-oxo-5-phenylcyclohexane-1-carbonitrile Chemical compound C1(=CC=CC=C1)C1(CC(C(CC1)=O)C#N)N QNKKWFGKBDIZCJ-UHFFFAOYSA-N 0.000 abstract 1
- AUBSNQATYLOWDD-UHFFFAOYSA-N 5-nitro-2-oxo-5-phenylcyclohexane-1-carbonitrile Chemical compound C1(=CC=CC=C1)C1(CC(C(CC1)=O)C#N)[N+](=O)[O-] AUBSNQATYLOWDD-UHFFFAOYSA-N 0.000 abstract 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 abstract 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 abstract 1
- VEYLYPMCBAGFFA-UHFFFAOYSA-N Cl.C1(=CC=CC=C1)C1(CCC(CC1)Cl)N Chemical compound Cl.C1(=CC=CC=C1)C1(CCC(CC1)Cl)N VEYLYPMCBAGFFA-UHFFFAOYSA-N 0.000 abstract 1
- PAFZNILMFXTMIY-UHFFFAOYSA-N Cyclohexylamine Natural products NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 abstract 1
- QQZWEECEMNQSTG-UHFFFAOYSA-N Ethyl nitrite Chemical compound CCON=O QQZWEECEMNQSTG-UHFFFAOYSA-N 0.000 abstract 1
- 239000001828 Gelatine Substances 0.000 abstract 1
- 229930194542 Keto Natural products 0.000 abstract 1
- CBIUBPLFYVQQRM-UHFFFAOYSA-N N=C=O.C1CCCCC1C1=CC=CC=C1 Chemical compound N=C=O.C1CCCCC1C1=CC=CC=C1 CBIUBPLFYVQQRM-UHFFFAOYSA-N 0.000 abstract 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 1
- 229910021626 Tin(II) chloride Inorganic materials 0.000 abstract 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 abstract 1
- 238000005903 acid hydrolysis reaction Methods 0.000 abstract 1
- 125000004442 acylamino group Chemical group 0.000 abstract 1
- 125000005262 alkoxyamine group Chemical group 0.000 abstract 1
- 239000000908 ammonium hydroxide Substances 0.000 abstract 1
- 150000001540 azides Chemical class 0.000 abstract 1
- NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 abstract 1
- 238000009835 boiling Methods 0.000 abstract 1
- 239000004202 carbamide Substances 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 239000000969 carrier Substances 0.000 abstract 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- 239000008298 dragée Substances 0.000 abstract 1
- 125000004185 ester group Chemical group 0.000 abstract 1
- 239000000796 flavoring agent Substances 0.000 abstract 1
- 235000013355 food flavoring agent Nutrition 0.000 abstract 1
- 229920000159 gelatin Polymers 0.000 abstract 1
- 235000019322 gelatine Nutrition 0.000 abstract 1
- 230000002140 halogenating effect Effects 0.000 abstract 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 abstract 1
- JUINSXZKUKVTMD-UHFFFAOYSA-N hydrogen azide Chemical compound N=[N+]=[N-] JUINSXZKUKVTMD-UHFFFAOYSA-N 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 239000012948 isocyanate Substances 0.000 abstract 1
- 150000002513 isocyanates Chemical class 0.000 abstract 1
- 150000002540 isothiocyanates Chemical class 0.000 abstract 1
- 235000015110 jellies Nutrition 0.000 abstract 1
- 125000000468 ketone group Chemical group 0.000 abstract 1
- AHNJTQYTRPXLLG-UHFFFAOYSA-N lithium;diethylazanide Chemical compound [Li+].CC[N-]CC AHNJTQYTRPXLLG-UHFFFAOYSA-N 0.000 abstract 1
- 150000007522 mineralic acids Chemical class 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 231100000252 nontoxic Toxicity 0.000 abstract 1
- 230000003000 nontoxic effect Effects 0.000 abstract 1
- 150000007524 organic acids Chemical class 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 238000007911 parenteral administration Methods 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 239000003755 preservative agent Substances 0.000 abstract 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 abstract 1
- VGTPCRGMBIAPIM-UHFFFAOYSA-M sodium thiocyanate Chemical compound [Na+].[S-]C#N VGTPCRGMBIAPIM-UHFFFAOYSA-M 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
- 239000007921 spray Substances 0.000 abstract 1
- 239000001119 stannous chloride Substances 0.000 abstract 1
- 235000011150 stannous chloride Nutrition 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 239000001117 sulphuric acid Substances 0.000 abstract 1
- 235000011149 sulphuric acid Nutrition 0.000 abstract 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 abstract 1
- 238000010792 warming Methods 0.000 abstract 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/13—Amines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/4841—Filling excipients; Inactive ingredients
- A61K9/4858—Organic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/33—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C211/34—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of a saturated carbon skeleton
- C07C211/35—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of a saturated carbon skeleton containing only non-condensed rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
1-Phenylcyclohexylamine is prepared (1) by treating 1-phenylcyclohexane carboxylic acid with hydrazoic acid in a strong mineral acid; (2) by treating 1-phenylcyclohexane carboxamide with an alkali metal hypohalite and subjecting the resulting isocyanate to acid hydrolysis; (3) by reacting an alkyl 1-phenylcyclohexane carboxylate with hydrazine, reacting the hydrazide so produced with nitrous acid, treating the azide so obtained with an aliphatic alcohol containing 1 to 4 carbon atoms and treating the resulting N-(1-phenylcyclohexyl)-carbamic acid alkyl ester with a strong mineral acid; (4) by reacting a 1-phenylcyclohexane alkali metal compound or magnesium halide with a haloamine or alkoxyamine under anhydrous conditions, advantageously in an inert organic solvent; (5) by hydrolysing a 1-phenylcyclohexane isocyanate or isothiocyanate or acylamino, urea or N-carboalkoxyamino compound, preferably with a mineral acid; (6) by reducing 1-phenylcyclohexyl hydrazine which may be further substituted on the nitrogen atoms, advantageously by catalytic hydrogenation; (7) by reducing a 1-phenyl-(halo-substituted)-cyclohexylamine, itself prepared by halogenating e.g. with thionyl chloride, a corresponding hydroxy-substituted compound the reduction being performed, for example, with lithium aluminium hydride or catalytically; (8) by reducing a 1-phenyl-(keto-substituted)-cyclohexylamine e.g. with hydrazine hydrate and alkali, or with lithium aluminium hydride to the hydroxy substituted compound, the keto compound itself being prepared for example by boiling with aqueous alkali a 1-phenyl-(keto-substituted)- cyclohexylamine containing as a substituent adjacent to the keto group a cyano, carboxyl or ester group; (9) by reacting a compound of the formula Me-(CH2)5-Me, wherein Me is an alkali metal or magnesium halide, with benzonitrile under anhydrous conditions and decomposing the resulting product with water; and (10) by catalytically hydrogenating N-benzyl-1-phenyl-cyclohexylamine. Examples illustrate each of the above processes. Salts of the product with organic and inorganic acids are described. 1-Phenyl-cyclohexane carboxamide is prepared from the acid chloride (itself prepared from the acid and thionyl chloride) and ammonium hydroxide. Methyl 1-phenyl cyclohexane carboxylate is prepared from the acid chloride and methanol. 1-Phenyl cyclohexyl isothiocyanate is prepared by warming 1-phenylcyclohexene with sodium thiocyanate and sulphuric acid. 1-Phenyl-1-methyl-2-(1-phenylcyclohexyl) - hydrazine is prepared by refluxing 1-methyl-1-phenyl-hydrazine with cyclohexanone in benzene, concentrating, refluxing with phenyl lithium in ether and decomposing with water. 2-Amino-2-phenyl-cyclohexanone is prepared by reacting 2-phenyl-cyclohexanone with ethyl nitrite in presence of sodium ethoxide to give 2-phenyl-2-nitroso-cyclohexanone and reducing this with stannous chloride. 1-Phenyl-4-chloro-cyclohexylamine hydrochloride is prepared by reacting acrylonitrile with a -nitro-toluene in presence of benzyl-trimethylammonium hydroxide to give bis-[a -(2-cyanoethyl)]-a -nitro-toluene, cyclizing this with lithium diethylamide to give 4-phenyl-4-nitro-2-cyanocyclohexanone, catalytically reducing this to 4-phenyl-4-amino-2-cyano-cyclohexanone, refluxing this with hydrochloric acid to give 4-amino-4-phenyl-cyclohexanone, reducing this with Li-A1H4 to 4-amino-4-phenyl-cyclohexanol and reacting this with thionyl chloride. N-Benzyl-l-phenyl-cyclohexylamine is prepared by refluxing benzylamine with cyclohexanone in toluene and then reacting with phenyl lithium and decomposing with water.ALSO:Pharmaceutical compositions comprise 1-phenylcyclohexylamine, hereinafter denoted as (X), or a non-toxic acid-addition salt thereof e.g. the hydrochloride +p-toluene-sulphonate and one of more conventional solid or liquid diluents or carriers, in the form of tablets, liquid or dry-filled capsules, aqueous or non-aqueous solutions-for oral or parenteral administration, dragees suppositories, inhalents, jellies or sprays, and the compositions may also contain preservatives or flavouring agents. Specific examples relate to aqueous liquid preparations, tablets, hard and soft gelatine capsules, ampoules (aqueous and oil solutions), suppositories.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US853775XA | 1957-09-19 | 1957-09-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB853775A true GB853775A (en) | 1960-11-09 |
Family
ID=22191224
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB6414/58A Expired GB853775A (en) | 1957-09-19 | 1958-02-27 | Pharmaceutical compositions and methods for producing phenylcyclohexane compounds |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB853775A (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3254124A (en) * | 1962-06-29 | 1966-05-31 | Parke Davis & Co | Aminoketones and methods for their production |
| WO1989009209A1 (en) * | 1988-03-25 | 1989-10-05 | Marion Laboratories, Inc. | Piperidine ring modified phencyclidine analogs as anticonvulsants |
| US11344510B2 (en) | 2019-12-26 | 2022-05-31 | Gilgamesh Pharmaceuticals, Inc. | Arylcyclohexylamine derivatives and their use in the treatment of psychiatric disorders |
| US11440879B2 (en) | 2020-02-18 | 2022-09-13 | Gilgamesh Pharmaceuticals, Inc. | Methods of treating mood disorders |
| US12129234B1 (en) | 2023-08-03 | 2024-10-29 | Gilgamesh Pharmaceuticals, Inc. | Crystalline salts of N-ethyl-(5-fluoro-1H-indol-3-yl)-N-methylethan-1-amine |
| US12157722B1 (en) | 2023-08-03 | 2024-12-03 | Gilgamesh Pharmaceuticals, Inc. | Crystalline hydrochloride salts of N-ethyl-2-(5-fluoro-1H-indol-3-yl)-N-methylethan-1-amine |
-
1958
- 1958-02-27 GB GB6414/58A patent/GB853775A/en not_active Expired
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3254124A (en) * | 1962-06-29 | 1966-05-31 | Parke Davis & Co | Aminoketones and methods for their production |
| WO1989009209A1 (en) * | 1988-03-25 | 1989-10-05 | Marion Laboratories, Inc. | Piperidine ring modified phencyclidine analogs as anticonvulsants |
| US11344510B2 (en) | 2019-12-26 | 2022-05-31 | Gilgamesh Pharmaceuticals, Inc. | Arylcyclohexylamine derivatives and their use in the treatment of psychiatric disorders |
| US11440879B2 (en) | 2020-02-18 | 2022-09-13 | Gilgamesh Pharmaceuticals, Inc. | Methods of treating mood disorders |
| US12129234B1 (en) | 2023-08-03 | 2024-10-29 | Gilgamesh Pharmaceuticals, Inc. | Crystalline salts of N-ethyl-(5-fluoro-1H-indol-3-yl)-N-methylethan-1-amine |
| US12157722B1 (en) | 2023-08-03 | 2024-12-03 | Gilgamesh Pharmaceuticals, Inc. | Crystalline hydrochloride salts of N-ethyl-2-(5-fluoro-1H-indol-3-yl)-N-methylethan-1-amine |
| US12180158B1 (en) | 2023-08-03 | 2024-12-31 | Gilgamesh Pharmaceuticals, Inc. | Crystalline fumarate salts of n-ethyl-2-(5-fluoro-1H-indol-3-yl)-n-methylethan-1-amine |
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