IE46910B1 - Fluorinated alkylamines and process for preparing same - Google Patents
Fluorinated alkylamines and process for preparing sameInfo
- Publication number
- IE46910B1 IE46910B1 IE1076/78A IE107678A IE46910B1 IE 46910 B1 IE46910 B1 IE 46910B1 IE 1076/78 A IE1076/78 A IE 1076/78A IE 107678 A IE107678 A IE 107678A IE 46910 B1 IE46910 B1 IE 46910B1
- Authority
- IE
- Ireland
- Prior art keywords
- compound
- formula
- fluoromethyl
- hooc
- hcl
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims 2
- 150000003973 alkyl amines Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 48
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 7
- 125000001589 carboacyl group Chemical group 0.000 claims abstract description 5
- 239000001257 hydrogen Substances 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 5
- 230000008569 process Effects 0.000 claims description 4
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 230000002401 inhibitory effect Effects 0.000 abstract description 6
- -1 3-carboxy-3- aminopropyl Chemical group 0.000 abstract description 5
- 229940066769 systemic antihistamines substituted alkylamines Drugs 0.000 abstract description 5
- 125000000143 2-carboxyethyl group Chemical group [H]OC(=O)C([H])([H])C([H])([H])* 0.000 abstract 1
- BCNUXXXHEIUHJB-UHFFFAOYSA-N 3-methyleneindolenine Chemical compound C1=CC=C2C(=C)C=NC2=C1 BCNUXXXHEIUHJB-UHFFFAOYSA-N 0.000 abstract 1
- FGPJTNGWZSJADQ-UHFFFAOYSA-N 3-methylideneindol-5-ol Chemical compound OC1=CC=C2N=CC(=C)C2=C1 FGPJTNGWZSJADQ-UHFFFAOYSA-N 0.000 abstract 1
- YLVJJWMZNUDZEO-UHFFFAOYSA-N 4-methylideneimidazole Chemical compound C=C1C=NC=N1 YLVJJWMZNUDZEO-UHFFFAOYSA-N 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- VUWZPRWSIVNGKG-UHFFFAOYSA-N fluoromethane Chemical compound F[CH2] VUWZPRWSIVNGKG-UHFFFAOYSA-N 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 125000006289 hydroxybenzyl group Chemical group 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 19
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
- 229910001868 water Inorganic materials 0.000 description 12
- 229960003638 dopamine Drugs 0.000 description 11
- 239000007789 gas Substances 0.000 description 11
- 230000015572 biosynthetic process Effects 0.000 description 10
- 229960001340 histamine Drugs 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 102000004031 Carboxy-Lyases Human genes 0.000 description 7
- 108090000489 Carboxy-Lyases Proteins 0.000 description 7
- 150000001412 amines Chemical class 0.000 description 7
- 238000001816 cooling Methods 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 238000010828 elution Methods 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 238000011282 treatment Methods 0.000 description 6
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 5
- 238000006114 decarboxylation reaction Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 239000003729 cation exchange resin Substances 0.000 description 4
- 150000003840 hydrochlorides Chemical class 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- WTDRDQBEARUVNC-LURJTMIESA-N L-DOPA Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-LURJTMIESA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- RBHJBMIOOPYDBQ-UHFFFAOYSA-N carbon dioxide;propan-2-one Chemical compound O=C=O.CC(C)=O RBHJBMIOOPYDBQ-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- GIKNHHRFLCDOEU-UHFFFAOYSA-N 4-(2-aminopropyl)phenol Chemical compound CC(N)CC1=CC=C(O)C=C1 GIKNHHRFLCDOEU-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- WTDRDQBEARUVNC-UHFFFAOYSA-N L-Dopa Natural products OC(=O)C(N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 235000011089 carbon dioxide Nutrition 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 2
- 230000003389 potentiating effect Effects 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- DZGWFCGJZKJUFP-UHFFFAOYSA-N tyramine Chemical compound NCCC1=CC=C(O)C=C1 DZGWFCGJZKJUFP-UHFFFAOYSA-N 0.000 description 2
- ZQISRDCJNBUVMM-RXMQYKEDSA-N (2r)-2-amino-3-(1h-imidazol-5-yl)propan-1-ol Chemical compound OC[C@H](N)CC1=CN=CN1 ZQISRDCJNBUVMM-RXMQYKEDSA-N 0.000 description 1
- UDQCRUSSQAXPJY-SECBINFHSA-N (2r)-2-amino-3-(1h-indol-3-yl)propan-1-ol Chemical compound C1=CC=C2C(C[C@H](CO)N)=CNC2=C1 UDQCRUSSQAXPJY-SECBINFHSA-N 0.000 description 1
- KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 description 1
- HJMZBGJRFDAOQO-UHFFFAOYSA-N 4-amino-5-fluoropentanoic acid;hydrochloride Chemical compound Cl.FCC(N)CCC(O)=O HJMZBGJRFDAOQO-UHFFFAOYSA-N 0.000 description 1
- ABSTXSZPGHDTAF-UHFFFAOYSA-N 4-amino-pentanoic acid Chemical compound CC(N)CCC(O)=O ABSTXSZPGHDTAF-UHFFFAOYSA-N 0.000 description 1
- JXSIMEWQEWYRDJ-UHFFFAOYSA-N 4-azaniumyl-5-fluoropentanoate Chemical compound FCC(N)CCC(O)=O JXSIMEWQEWYRDJ-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 102100038238 Aromatic-L-amino-acid decarboxylase Human genes 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- WTDRDQBEARUVNC-ZCFIWIBFSA-N D-DOPA Chemical compound OC(=O)[C@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-ZCFIWIBFSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical class OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 102000008214 Glutamate decarboxylase Human genes 0.000 description 1
- 108091022930 Glutamate decarboxylase Proteins 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 208000001953 Hypotension Diseases 0.000 description 1
- 229920004459 Kel-F® PCTFE Polymers 0.000 description 1
- ZQISRDCJNBUVMM-UHFFFAOYSA-N L-Histidinol Natural products OCC(N)CC1=CN=CN1 ZQISRDCJNBUVMM-UHFFFAOYSA-N 0.000 description 1
- ZQISRDCJNBUVMM-YFKPBYRVSA-N L-histidinol Chemical compound OC[C@@H](N)CC1=CNC=N1 ZQISRDCJNBUVMM-YFKPBYRVSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 208000018737 Parkinson disease Diseases 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 239000000150 Sympathomimetic Substances 0.000 description 1
- 108010035075 Tyrosine decarboxylase Proteins 0.000 description 1
- 208000025865 Ulcer Diseases 0.000 description 1
- 239000011358 absorbing material Substances 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 150000001370 alpha-amino acid derivatives Chemical class 0.000 description 1
- 235000008206 alpha-amino acids Nutrition 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 229940025084 amphetamine Drugs 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 229910052925 anhydrite Inorganic materials 0.000 description 1
- 230000001430 anti-depressive effect Effects 0.000 description 1
- 230000003276 anti-hypertensive effect Effects 0.000 description 1
- 239000000935 antidepressant agent Substances 0.000 description 1
- 229940005513 antidepressants Drugs 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 230000006696 biosynthetic metabolic pathway Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 235000011148 calcium chloride Nutrition 0.000 description 1
- 229960004424 carbon dioxide Drugs 0.000 description 1
- 150000003943 catecholamines Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- UUAGAQFQZIEFAH-UHFFFAOYSA-N chlorotrifluoroethylene Chemical compound FC(F)=C(F)Cl UUAGAQFQZIEFAH-UHFFFAOYSA-N 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 239000013256 coordination polymer Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000003954 decarboxylase inhibitor Substances 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- MHUWZNTUIIFHAS-CLFAGFIQSA-N dioleoyl phosphatidic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(COP(O)(O)=O)OC(=O)CCCCCCC\C=C/CCCCCCCC MHUWZNTUIIFHAS-CLFAGFIQSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000012156 elution solvent Substances 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- INCWELKXTZCRSA-UHFFFAOYSA-N ethyl acetate;methanol;hydrate Chemical compound O.OC.CCOC(C)=O INCWELKXTZCRSA-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- BYVCDJVESPBRQW-UHFFFAOYSA-N fluoromethanamine Chemical class NCF BYVCDJVESPBRQW-UHFFFAOYSA-N 0.000 description 1
- 229960003692 gamma aminobutyric acid Drugs 0.000 description 1
- 229960004931 histamine dihydrochloride Drugs 0.000 description 1
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 1
- GPGMRSSBVJNWRA-UHFFFAOYSA-N hydrochloride hydrofluoride Chemical compound F.Cl GPGMRSSBVJNWRA-UHFFFAOYSA-N 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229950005360 hydroxyamfetamine Drugs 0.000 description 1
- 230000036543 hypotension Effects 0.000 description 1
- 238000000099 in vitro assay Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 229960004502 levodopa Drugs 0.000 description 1
- 238000003760 magnetic stirring Methods 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- MLSKXPOBNQFGHW-UHFFFAOYSA-N methoxy(dioxido)borane Chemical compound COB([O-])[O-] MLSKXPOBNQFGHW-UHFFFAOYSA-N 0.000 description 1
- 238000004452 microanalysis Methods 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000036584 pressor response Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- QHMQWEPBXSHHLH-UHFFFAOYSA-N sulfur tetrafluoride Chemical compound FS(F)(F)F QHMQWEPBXSHHLH-UHFFFAOYSA-N 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 229940127230 sympathomimetic drug Drugs 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- SMBZJSVIKJMSFP-UHFFFAOYSA-N trifluoromethyl hypofluorite Chemical compound FOC(F)(F)F SMBZJSVIKJMSFP-UHFFFAOYSA-N 0.000 description 1
- 229960003732 tyramine Drugs 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/02—Non-specific cardiovascular stimulants, e.g. drugs for syncope, antihypotensives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
- C07D209/16—Tryptamines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Cardiology (AREA)
- Pharmacology & Pharmacy (AREA)
- Heart & Thoracic Surgery (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US80235077A | 1977-06-01 | 1977-06-01 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE781076L IE781076L (en) | 1978-12-01 |
| IE46910B1 true IE46910B1 (en) | 1983-11-02 |
Family
ID=25183471
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE1076/78A IE46910B1 (en) | 1977-06-01 | 1978-05-30 | Fluorinated alkylamines and process for preparing same |
Country Status (6)
| Country | Link |
|---|---|
| EP (1) | EP0000036B1 (enrdf_load_stackoverflow) |
| JP (1) | JPS5416422A (enrdf_load_stackoverflow) |
| DE (1) | DE2861148D1 (enrdf_load_stackoverflow) |
| DK (1) | DK240578A (enrdf_load_stackoverflow) |
| IE (1) | IE46910B1 (enrdf_load_stackoverflow) |
| IT (1) | IT1104712B (enrdf_load_stackoverflow) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU3872678A (en) * | 1977-09-01 | 1980-02-14 | Merrell Toraude & Co | Alpha-halomethyl amines |
| US4326071A (en) * | 1977-09-28 | 1982-04-20 | Merrell Toraude Et Compagnie | Halomethyl derivatives of gamma-aminobutyric acid and related compounds |
| ZA785435B (en) * | 1977-10-19 | 1979-09-26 | Merrell Toraude & Co | A-halomethyl derivatives of histamine and related compounds |
| NZ194348A (en) * | 1979-07-26 | 1982-09-14 | Merrell Toraude & Co | Fluorinated methyl-beta-alanine derivatives and pharmaceutical compositions |
| US4542802A (en) * | 1982-04-02 | 1985-09-24 | Woodward Governor Company | Engine and transmission control system for combines and the like |
| CA1302919C (en) * | 1985-07-03 | 1992-06-09 | Robert T. Buckler | Histamine derivatives, immunogen conjugates and antibodies raised thereto |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR104F (enrdf_load_stackoverflow) * | 1960-11-05 | |||
| GB1218135A (en) * | 1967-07-28 | 1971-01-06 | Abbott Lab | Substituted phenethylamine derivatives |
| US3839170A (en) * | 1970-08-03 | 1974-10-01 | Merck & Co Inc | Process for the preparation of 3-fluoro-d-alanine |
-
1978
- 1978-05-30 IE IE1076/78A patent/IE46910B1/en unknown
- 1978-05-31 DK DK240578A patent/DK240578A/da not_active Application Discontinuation
- 1978-05-31 IT IT49634/78A patent/IT1104712B/it active
- 1978-06-01 EP EP78100059A patent/EP0000036B1/en not_active Expired
- 1978-06-01 JP JP6501478A patent/JPS5416422A/ja active Granted
- 1978-06-01 DE DE7878100059T patent/DE2861148D1/de not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| IE781076L (en) | 1978-12-01 |
| IT7849634A0 (it) | 1978-05-31 |
| IT1104712B (it) | 1985-10-28 |
| EP0000036B1 (en) | 1981-10-14 |
| DK240578A (da) | 1978-12-02 |
| JPS6123177B2 (enrdf_load_stackoverflow) | 1986-06-04 |
| JPS5416422A (en) | 1979-02-07 |
| DE2861148D1 (en) | 1981-12-24 |
| EP0000036A1 (en) | 1978-12-20 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4325961A (en) | Fluorinated amino acids | |
| Bey et al. | Direct synthesis of. alpha.-halogenomethyl-. alpha.-amino acids from the parent. alpha.-amino acids | |
| HK63992A (en) | 1-phenyl-3-naphthalenyloxy-propanamines | |
| WO1996002492A1 (en) | Method of making a benzylpropanamine | |
| CA1269997A (en) | Racemization process | |
| FI66840B (fi) | Foerfarande foer framstaellning av nya terapeutiskt anvaendbara alfa-fluormetyl-alfa-aminoalkansyror | |
| IE46910B1 (en) | Fluorinated alkylamines and process for preparing same | |
| FR2776660A1 (fr) | Diazepino-indoles de phosphodiesterases iv | |
| US4695588A (en) | Fluorinated amino acids | |
| JP4542208B2 (ja) | α―アミノ酸アミド、その製造方法及びその治療的使用 | |
| AU733001B2 (en) | 5-hydroxymethyl-2-aminotetralins as cardiovascular agents | |
| US4431817A (en) | Fluorinated imidazolyl alkylamines | |
| US4431821A (en) | Fluorinated tryptamines | |
| EP0000034B1 (en) | Fluorinated amines, compositions and process for preparing said compounds | |
| de Meijere et al. | Convenient Syntheses of Novel α‐and β‐Amino Acids with Spiropentyl Groups | |
| SK10632003A3 (sk) | Inhibítor príjmu monoamínov | |
| US5102914A (en) | Antihypertensive sulfonanilides | |
| Van Dort et al. | Synthesis and carbon‐11 labeling of the stereoisomers of meta‐hydroxyephedrine (HED) and meta‐hydroxypseudoephedrine (HPED) | |
| US4148919A (en) | 7-Amino-6,7-dihydro [5H]benzocycloheptene derivatives | |
| JPH0341459B2 (enrdf_load_stackoverflow) | ||
| Florvall et al. | Prodrugs of neuron-selective monoamine oxidase inhibitors: amino acid derivatives of 1-(4-aminophenyl)-2-aminopropanes | |
| EP0293351B1 (en) | New aralkyl esters and processes for their preparation | |
| EP0027993A1 (en) | 6-Fluorodihydroxyphenylalanines, a process for preparing and a pharmaceutical composition containing the same | |
| Secor et al. | Synthesis of [methyl‐14C]‐N‐methylputrescine | |
| JPH02121953A (ja) | シクロアルキル置換４―アミノフェニル誘導体およびその製造方法 |