CH625795A5 - - Google Patents

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Publication number: CH625795A5
Authority: CH; Switzerland
Prior art keywords: trifluoromethyl; general formula; oxazoline; radical; acid
Prior art date: 1976-05-24

Application number

CH632677A

Other languages

English (en)

French (fr)

Inventor

Charles Malen

Pierre Roger

Michel Laubie

Original Assignee

Science Union & Cie

Priority date (The priority date 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 date listed.)

1976-05-24

Filing date

1977-05-23

Publication date

1981-10-15

1977-05-23 Application filed by Science Union & Cie filed Critical Science Union & Cie

1981-10-15 Publication of CH625795A5 publication Critical patent/CH625795A5/fr

Links

238000000034 method Methods 0.000 claims description 34
-1 alkoxy radical Chemical class 0.000 claims description 32
150000001875 compounds Chemical class 0.000 claims description 30
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 29
IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 claims description 22
150000001412 amines Chemical class 0.000 claims description 18
125000001424 substituent group Chemical group 0.000 claims description 16
229910052739 hydrogen Inorganic materials 0.000 claims description 14
239000001257 hydrogen Substances 0.000 claims description 13
239000000460 chlorine Substances 0.000 claims description 11
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
239000002253 acid Substances 0.000 claims description 8
150000002431 hydrogen Chemical group 0.000 claims description 8
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 8
229910052500 inorganic mineral Inorganic materials 0.000 claims description 7
239000012948 isocyanate Substances 0.000 claims description 7
150000002513 isocyanates Chemical class 0.000 claims description 7
239000011707 mineral Substances 0.000 claims description 7
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
150000007522 mineralic acids Chemical class 0.000 claims description 6
150000007524 organic acids Chemical class 0.000 claims description 6
229910052717 sulfur Chemical group 0.000 claims description 6
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
229910052801 chlorine Inorganic materials 0.000 claims description 5
QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims description 5
238000010438 heat treatment Methods 0.000 claims description 5
229910052760 oxygen Inorganic materials 0.000 claims description 5
239000001301 oxygen Substances 0.000 claims description 5
150000003839 salts Chemical class 0.000 claims description 5
239000011593 sulfur Chemical group 0.000 claims description 5
XIPUIGPNIDKXJU-UHFFFAOYSA-N [CH]1CC1 Chemical compound [CH]1CC1 XIPUIGPNIDKXJU-UHFFFAOYSA-N 0.000 claims description 4
125000003545 alkoxy group Chemical group 0.000 claims description 4
125000003118 aryl group Chemical group 0.000 claims description 4
229910052794 bromium Inorganic materials 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 4
150000002540 isothiocyanates Chemical class 0.000 claims description 4
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 4
238000002360 preparation method Methods 0.000 claims description 4
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 3
125000004423 acyloxy group Chemical group 0.000 claims description 3
125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims description 3
229910052740 iodine Inorganic materials 0.000 claims description 3
230000003287 optical effect Effects 0.000 claims description 3
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical compound F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 claims description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
229910000288 alkali metal carbonate Inorganic materials 0.000 claims description 2
150000008041 alkali metal carbonates Chemical class 0.000 claims description 2
239000012736 aqueous medium Substances 0.000 claims description 2
238000009833 condensation Methods 0.000 claims description 2
230000005494 condensation Effects 0.000 claims description 2
150000004292 cyclic ethers Chemical class 0.000 claims description 2
239000012442 inert solvent Substances 0.000 claims description 2
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 2
238000007363 ring formation reaction Methods 0.000 claims description 2
125000005270 trialkylamine group Chemical group 0.000 claims description 2
DBCGDMLNSRGMLI-UHFFFAOYSA-N n-benzyl-4,5-dihydro-1,3-oxazol-2-amine Chemical class C=1C=CC=CC=1CNC1=NCCO1 DBCGDMLNSRGMLI-UHFFFAOYSA-N 0.000 claims 1
235000005985 organic acids Nutrition 0.000 claims 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 26
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 21
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 20
238000004458 analytical method Methods 0.000 description 18
239000000243 solution Substances 0.000 description 16
239000000047 product Substances 0.000 description 15
239000004202 carbamide Substances 0.000 description 14
239000000155 melt Substances 0.000 description 13
238000002844 melting Methods 0.000 description 13
230000008018 melting Effects 0.000 description 13
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
239000000203 mixture Substances 0.000 description 11
HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 10
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 10
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
238000001953 recrystallisation Methods 0.000 description 8
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
FEWJPZIEWOKRBE-LWMBPPNESA-N levotartaric acid Chemical compound OC(=O)[C@@H](O)[C@H](O)C(O)=O FEWJPZIEWOKRBE-LWMBPPNESA-N 0.000 description 7
238000000859 sublimation Methods 0.000 description 7
230000008022 sublimation Effects 0.000 description 7
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 6
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
238000002329 infrared spectrum Methods 0.000 description 6
239000002904 solvent Substances 0.000 description 6
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 5
239000000706 filtrate Substances 0.000 description 5
150000002923 oximes Chemical class 0.000 description 5
239000002244 precipitate Substances 0.000 description 5
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 4
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
229910000147 aluminium phosphate Inorganic materials 0.000 description 4
239000003153 chemical reaction reagent Substances 0.000 description 4
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 4
238000010992 reflux Methods 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
241001465754 Metazoa Species 0.000 description 3
125000000217 alkyl group Chemical group 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
238000001914 filtration Methods 0.000 description 3
VBZWSGALLODQNC-UHFFFAOYSA-N hexafluoroacetone Chemical compound FC(F)(F)C(=O)C(F)(F)F VBZWSGALLODQNC-UHFFFAOYSA-N 0.000 description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
239000007788 liquid Substances 0.000 description 3
JXHZJFSDXHTECM-UHFFFAOYSA-N n-[2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethylidene]hydroxylamine Chemical compound ON=C(C(F)(F)F)C1=CC=CC(C(F)(F)F)=C1 JXHZJFSDXHTECM-UHFFFAOYSA-N 0.000 description 3
239000012071 phase Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
MDCHHRZBYSSONX-UHFFFAOYSA-N 2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethanone Chemical compound FC(F)(F)C(=O)C1=CC=CC(C(F)(F)F)=C1 MDCHHRZBYSSONX-UHFFFAOYSA-N 0.000 description 2
BITBMHVXCILUEX-UHFFFAOYSA-N 2-chloroethylurea Chemical compound NC(=O)NCCCl BITBMHVXCILUEX-UHFFFAOYSA-N 0.000 description 2
125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 2
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
206010035039 Piloerection Diseases 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
206010039897 Sedation Diseases 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
230000007059 acute toxicity Effects 0.000 description 2
231100000403 acute toxicity Toxicity 0.000 description 2
238000013019 agitation Methods 0.000 description 2
GZCGUPFRVQAUEE-SLPGGIOYSA-N aldehydo-D-glucose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O GZCGUPFRVQAUEE-SLPGGIOYSA-N 0.000 description 2
229910000102 alkali metal hydride Inorganic materials 0.000 description 2
150000008046 alkali metal hydrides Chemical class 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
125000004429 atom Chemical group 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
230000036772 blood pressure Effects 0.000 description 2
229910052793 cadmium Inorganic materials 0.000 description 2
239000002775 capsule Substances 0.000 description 2
238000001816 cooling Methods 0.000 description 2
239000013256 coordination polymer Substances 0.000 description 2
239000012043 crude product Substances 0.000 description 2
229960001270 d- tartaric acid Drugs 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
229910052731 fluorine Inorganic materials 0.000 description 2
238000004508 fractional distillation Methods 0.000 description 2
JMANVNJQNLATNU-UHFFFAOYSA-N glycolonitrile Natural products N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 description 2
229910052736 halogen Inorganic materials 0.000 description 2
150000002367 halogens Chemical class 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
125000004356 hydroxy functional group Chemical group O* 0.000 description 2
230000001077 hypotensive effect Effects 0.000 description 2
239000002198 insoluble material Substances 0.000 description 2
SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 2
231100000636 lethal dose Toxicity 0.000 description 2
239000012280 lithium aluminium hydride Substances 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
230000000926 neurological effect Effects 0.000 description 2
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 2
239000008194 pharmaceutical composition Substances 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
230000005371 pilomotor reflex Effects 0.000 description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
230000036280 sedation Effects 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
239000007858 starting material Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
229960001367 tartaric acid Drugs 0.000 description 2
239000011975 tartaric acid Substances 0.000 description 2
235000002906 tartaric acid Nutrition 0.000 description 2
CBDKQYKMCICBOF-UHFFFAOYSA-N thiazoline Chemical compound C1CN=CS1 CBDKQYKMCICBOF-UHFFFAOYSA-N 0.000 description 2
150000003585 thioureas Chemical class 0.000 description 2
QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 2
XJLSEXAGTJCILF-RXMQYKEDSA-N (R)-nipecotic acid zwitterion Chemical compound OC(=O)[C@@H]1CCCNC1 XJLSEXAGTJCILF-RXMQYKEDSA-N 0.000 description 1
UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
YZVFSQQHQPPKNX-UHFFFAOYSA-N 1,3-thiazole-5-carboxylic acid Chemical compound OC(=O)C1=CN=CS1 YZVFSQQHQPPKNX-UHFFFAOYSA-N 0.000 description 1
DYPQUENOGZXOGE-UHFFFAOYSA-N 1-(4-chlorophenyl)-2,2,2-trifluoroethanone Chemical compound FC(F)(F)C(=O)C1=CC=C(Cl)C=C1 DYPQUENOGZXOGE-UHFFFAOYSA-N 0.000 description 1
OXHNLMTVIGZXSG-UHFFFAOYSA-N 1-Methylpyrrole Chemical compound CN1C=CC=C1 OXHNLMTVIGZXSG-UHFFFAOYSA-N 0.000 description 1
NCJZVRPXSSYDBG-UHFFFAOYSA-N 2,2,2-trifluoro-1-(4-methoxyphenyl)ethanone Chemical compound COC1=CC=C(C(=O)C(F)(F)F)C=C1 NCJZVRPXSSYDBG-UHFFFAOYSA-N 0.000 description 1
MAZDPKNERLXXOV-UHFFFAOYSA-N 2,2,2-trifluoro-1-(furan-2-yl)ethanone Chemical compound FC(F)(F)C(=O)C1=CC=CO1 MAZDPKNERLXXOV-UHFFFAOYSA-N 0.000 description 1
DZCAUMADOBDJJH-UHFFFAOYSA-N 2,2,2-trifluoro-1-phenylethanamine Chemical compound FC(F)(F)C(N)C1=CC=CC=C1 DZCAUMADOBDJJH-UHFFFAOYSA-N 0.000 description 1
VUBUXALTYMBEQO-UHFFFAOYSA-N 2,2,3,3,3-pentafluoro-1-phenylpropan-1-one Chemical compound FC(F)(F)C(F)(F)C(=O)C1=CC=CC=C1 VUBUXALTYMBEQO-UHFFFAOYSA-N 0.000 description 1
JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 description 1
KGWNRZLPXLBMPS-UHFFFAOYSA-N 2h-1,3-oxazine Chemical compound C1OC=CC=N1 KGWNRZLPXLBMPS-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
BTXXTMOWISPQSJ-UHFFFAOYSA-N 4,4,4-trifluorobutan-2-one Chemical compound CC(=O)CC(F)(F)F BTXXTMOWISPQSJ-UHFFFAOYSA-N 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
BQACOLQNOUYJCE-FYZZASKESA-N Abietic acid Natural products CC(C)C1=CC2=CC[C@]3(C)[C@](C)(CCC[C@@]3(C)C(=O)O)[C@H]2CC1 BQACOLQNOUYJCE-FYZZASKESA-N 0.000 description 1
RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
LSPHULWDVZXLIL-UHFFFAOYSA-N Camphoric acid Natural products CC1(C)C(C(O)=O)CCC1(C)C(O)=O LSPHULWDVZXLIL-UHFFFAOYSA-N 0.000 description 1
241000282472 Canis lupus familiaris Species 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
RYECOJGRJDOGPP-UHFFFAOYSA-N Ethylurea Chemical compound CCNC(N)=O RYECOJGRJDOGPP-UHFFFAOYSA-N 0.000 description 1
241000282326 Felis catus Species 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
208000001953 Hypotension Diseases 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
241000699666 Mus <mouse, genus> Species 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
239000002262 Schiff base Substances 0.000 description 1
150000004753 Schiff bases Chemical class 0.000 description 1
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
NIJJYAXOARWZEE-UHFFFAOYSA-N Valproic acid Chemical compound CCCC(C(O)=O)CCC NIJJYAXOARWZEE-UHFFFAOYSA-N 0.000 description 1
238000005903 acid hydrolysis reaction Methods 0.000 description 1
230000010933 acylation Effects 0.000 description 1
238000005917 acylation reaction Methods 0.000 description 1
150000004791 alkyl magnesium halides Chemical class 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
239000002220 antihypertensive agent Substances 0.000 description 1
229940127088 antihypertensive drug Drugs 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
150000001491 aromatic compounds Chemical group 0.000 description 1
235000010323 ascorbic acid Nutrition 0.000 description 1
229960005070 ascorbic acid Drugs 0.000 description 1
239000011668 ascorbic acid Substances 0.000 description 1
230000002238 attenuated effect Effects 0.000 description 1
239000002585 base Substances 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
229940092714 benzenesulfonic acid Drugs 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
230000036760 body temperature Effects 0.000 description 1
230000036471 bradycardia Effects 0.000 description 1
208000006218 bradycardia Diseases 0.000 description 1
BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 1
LSPHULWDVZXLIL-QUBYGPBYSA-N camphoric acid Chemical compound CC1(C)[C@H](C(O)=O)CC[C@]1(C)C(O)=O LSPHULWDVZXLIL-QUBYGPBYSA-N 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
QPJDMGCKMHUXFD-UHFFFAOYSA-N cyanogen chloride Chemical compound ClC#N QPJDMGCKMHUXFD-UHFFFAOYSA-N 0.000 description 1
238000010908 decantation Methods 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
ZFLJBPPHKFQKJM-UHFFFAOYSA-N dinaphthalen-1-yl hydrogen phosphate Chemical compound C1=CC=C2C(OP(=O)(OC=3C4=CC=CC=C4C=CC=3)O)=CC=CC2=C1 ZFLJBPPHKFQKJM-UHFFFAOYSA-N 0.000 description 1
239000008298 dragée Substances 0.000 description 1
239000006196 drop Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
235000013305 food Nutrition 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
150000002366 halogen compounds Chemical class 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hcl hcl Chemical compound Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
150000002430 hydrocarbons Chemical group 0.000 description 1
XNXVOSBNFZWHBV-UHFFFAOYSA-N hydron;o-methylhydroxylamine;chloride Chemical compound Cl.CON XNXVOSBNFZWHBV-UHFFFAOYSA-N 0.000 description 1
150000002443 hydroxylamines Chemical class 0.000 description 1
230000036543 hypotension Effects 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
239000011630 iodine Substances 0.000 description 1
229940045996 isethionic acid Drugs 0.000 description 1
125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
239000002609 medium Substances 0.000 description 1
229910052753 mercury Inorganic materials 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
125000000896 monocarboxylic acid group Chemical group 0.000 description 1
210000003205 muscle Anatomy 0.000 description 1
YVQTYCGUGOVSCD-UHFFFAOYSA-N n-(1,1,1,3,3,3-hexafluoropropan-2-ylidene)hydroxylamine Chemical compound ON=C(C(F)(F)F)C(F)(F)F YVQTYCGUGOVSCD-UHFFFAOYSA-N 0.000 description 1
LIIIXURRQRBKTB-UHFFFAOYSA-N n-(2,2,3,3,3-pentafluoro-1-phenylpropylidene)hydroxylamine Chemical compound FC(F)(F)C(F)(F)C(=NO)C1=CC=CC=C1 LIIIXURRQRBKTB-UHFFFAOYSA-N 0.000 description 1
DHFHLGPVGBSNLI-UHFFFAOYSA-N n-[1-(4-chlorophenyl)-2,2,2-trifluoroethylidene]hydroxylamine Chemical compound ON=C(C(F)(F)F)C1=CC=C(Cl)C=C1 DHFHLGPVGBSNLI-UHFFFAOYSA-N 0.000 description 1
GTIRHANHGLHLIQ-UHFFFAOYSA-N n-[2,2,2-trifluoro-1-(4-methoxyphenyl)ethylidene]hydroxylamine Chemical compound COC1=CC=C(C(=NO)C(F)(F)F)C=C1 GTIRHANHGLHLIQ-UHFFFAOYSA-N 0.000 description 1
125000001298 n-hexoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
229940105631 nembutal Drugs 0.000 description 1
125000005484 neopentoxy group Chemical group 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
230000002474 noradrenergic effect Effects 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
125000002524 organometallic group Chemical group 0.000 description 1
150000002918 oxazolines Chemical class 0.000 description 1
125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
235000015277 pork Nutrition 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
238000000746 purification Methods 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
238000009987 spinning Methods 0.000 description 1
239000000021 stimulant Substances 0.000 description 1
239000006190 sub-lingual tablet Substances 0.000 description 1
125000004434 sulfur atom Chemical group 0.000 description 1
239000000829 suppository Substances 0.000 description 1
230000002889 sympathetic effect Effects 0.000 description 1
239000003826 tablet Substances 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
150000003549 thiazolines Chemical class 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
230000001052 transient effect Effects 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000003643 water by type Substances 0.000 description 1
238000005303 weighing Methods 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/33—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/333—Radicals substituted by oxygen or sulfur atoms
- 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
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/33—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/335—Radicals substituted by nitrogen atoms not forming part of a nitro radical
- 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
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
- C07D233/44—Nitrogen atoms not forming part of a nitro radical
- C07D233/48—Nitrogen atoms not forming part of a nitro radical with acyclic hydrocarbon or substituted acyclic hydrocarbon radicals, attached to said nitrogen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/06—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D239/08—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms directly attached in position 2
- C07D239/12—Nitrogen atoms not forming part of a nitro radical
- C07D239/14—Nitrogen atoms not forming part of a nitro radical with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to said nitrogen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
- C07D263/28—Nitrogen atoms not forming part of a nitro radical
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
- C07D265/06—1,3-Oxazines; Hydrogenated 1,3-oxazines not condensed with other rings
- C07D265/08—1,3-Oxazines; Hydrogenated 1,3-oxazines not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/08—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D277/12—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
- C07D277/18—Nitrogen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/20—Radicals substituted by singly bound hetero atoms other than halogen by nitrogen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/22—Radicals substituted by doubly bound hetero atoms, or by two hetero atoms other than halogen singly bound to the same carbon atom

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Life Sciences & Earth Sciences (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Engineering & Computer Science (AREA)
Pharmacology & Pharmacy (AREA)
Bioinformatics & Cheminformatics (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Plural Heterocyclic Compounds (AREA)
Thiazole And Isothizaole Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

CH632677A 1976-05-24 1977-05-23 CH625795A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
FR7615601A FR2358890A1 (fr)	1976-05-24	1976-05-24	Nouvelles aryl trifluoroethylamines, leurs procedes d'obtention et les compositions pharmaceutiques en renfermant

Publications (1)

Publication Number	Publication Date
CH625795A5 true CH625795A5 (de)	1981-10-15

Family

ID=9173528

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH632677A CH625795A5 (de)	1976-05-24	1977-05-23

Country Status (21)

Country	Link
US (3)	US4267345A (de)
JP (2)	JPS584715B2 (de)
AR (2)	AR219296A1 (de)
AT (1)	AT350062B (de)
AU (1)	AU517715B2 (de)
BE (1)	BE854908A (de)
CH (1)	CH625795A5 (de)
DE (1)	DE2723464C2 (de)
ES (1)	ES459086A1 (de)
FR (1)	FR2358890A1 (de)
GB (2)	GB1564269A (de)
GR (1)	GR61659B (de)
HU (1)	HU177039B (de)
IL (1)	IL52137A (de)
NL (1)	NL169182C (de)
NZ (1)	NZ184175A (de)
OA (1)	OA05668A (de)
PH (1)	PH13880A (de)
PT (1)	PT66584B (de)
SE (1)	SE7705986L (de)
SU (2)	SU725561A3 (de)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2444673A1 (fr) *	1978-12-20	1980-07-18	Science Union & Cie	Nouvelles trifluoroethylamines, leurs procedes d'obtention et leur emploi comme medicament
US4348247A (en) *	1979-02-26	1982-09-07	Rockwell International Corporation	Method of fabricating a reinforced tubular structure
ATE29494T1 (de) *	1983-08-11	1987-09-15	Synthelabo	Indol-derivate, verfahren zu deren herstellung und deren therapeutische anwendung.
JPH06312412A (ja) *	1992-06-10	1994-11-08	Nippon Hume Pipe Co Ltd	模様付き複合コンクリート製品およびその成形方法
AUPP020297A0 (en) *	1997-11-05	1997-11-27	University Of Melbourne, The	A novel receptor, and compounds which bind thereto
CA2443906A1 (en) *	2001-04-16	2002-10-24	University Of Virginia Patent Foundation	Novel oral general anesthetics and metabolitically resistant anticonvulsants
EP2070923A1 (de)	2007-12-11	2009-06-17	Bayer CropScience AG	Insektizide Iminoheterocyclen
UY32940A (es)	2009-10-27	2011-05-31	Bayer Cropscience Ag	Amidas sustituidas con halogenoalquilo como insecticidas y acaricidas
AR085509A1 (es)	2011-03-09	2013-10-09	Bayer Cropscience Ag	Indol- y bencimidazolcarboxamidas como insecticidas y acaricidas
US9345247B2 (en)	2012-08-17	2016-05-24	Bayer Cropscience Ag	Azaindole carboxylic acid amides and azaindole thiocarboxylic acid amides for use as insecticides and acaricides

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2889351A (en) *	1956-05-25	1959-06-02	Pfizer & Co C	Therapeutic agents
US3626067A (en) *	1965-07-01	1971-12-07	Du Pont	Substituted oxazolines, useful as pharmaceuticals
US3453284A (en) *	1966-01-19	1969-07-01	Du Pont	Certain 2-(substituted-anilino)-2-oxazolines
DE1670751A1 (de) *	1966-09-27	1970-12-23	Bayer Ag	Verfahren zur Herstellung von 2-Phenylamino-2-oxazolinen
US3622067A (en) *	1969-06-13	1971-11-23	Ok Partnership Ltd	Document coder
BE754832A (fr) *	1969-08-14	1971-02-15	Beecham Group Ltd	Iminazolines
USRE27133E (en)	1970-03-20	1971-06-01		Cdj)zco
US4102890A (en) *	1972-12-28	1978-07-25	Science-Union Et Cie, Societe Francaise De Recherche Medicale	2-Amino oxazolines and process for making the same
GB1453703A (en) *	1972-12-28	1976-10-27	Science Union & Cie	Substituted cyclopropylmethylamines processes for their preparation and pharmaceutical compositions containing them
FR2269341B1 (de) *	1974-04-30	1978-07-28	Castaigne Sa
GB1475513A (en) *	1974-06-20	1977-06-01	Science Union & Cie	Benzylamine derivatives process for science union et cie benzylamine derivatives process for their production and pharmaceutical compositions containing them

1976
- 1976-05-24 FR FR7615601A patent/FR2358890A1/fr active Granted
1977
- 1977-05-20 IL IL52137A patent/IL52137A/xx unknown
- 1977-05-23 SE SE7705986A patent/SE7705986L/xx unknown
- 1977-05-23 GB GB26511/78A patent/GB1564269A/en not_active Expired
- 1977-05-23 BE BE177800A patent/BE854908A/xx unknown
- 1977-05-23 AU AU25376/77A patent/AU517715B2/en not_active Expired
- 1977-05-23 PT PT66584A patent/PT66584B/pt unknown
- 1977-05-23 GB GB21613/77A patent/GB1564268A/en not_active Expired
- 1977-05-23 GR GR53532A patent/GR61659B/el unknown
- 1977-05-23 CH CH632677A patent/CH625795A5/fr not_active IP Right Cessation
- 1977-05-23 AT AT368277A patent/AT350062B/de not_active IP Right Cessation
- 1977-05-23 NZ NZ184175A patent/NZ184175A/xx unknown
- 1977-05-24 ES ES459086A patent/ES459086A1/es not_active Expired
- 1977-05-24 JP JP52060367A patent/JPS584715B2/ja not_active Expired
- 1977-05-24 NL NLAANVRAGE7705727,A patent/NL169182C/xx not_active IP Right Cessation
- 1977-05-24 HU HU77SI1577A patent/HU177039B/hu unknown
- 1977-05-24 AR AR267755A patent/AR219296A1/es active
- 1977-05-24 OA OA56177A patent/OA05668A/xx unknown
- 1977-05-24 DE DE2723464A patent/DE2723464C2/de not_active Expired
- 1977-05-24 SU SU772481553A patent/SU725561A3/ru active
- 1977-05-24 PH PH19810A patent/PH13880A/en unknown
1978
- 1978-10-18 AR AR274117A patent/AR222022A1/es active
- 1978-12-20 SU SU782699403A patent/SU791234A3/ru active
1979
- 1979-04-19 US US06/031,386 patent/US4267345A/en not_active Expired - Lifetime
1980
- 1980-02-22 JP JP2149380A patent/JPS55127390A/ja active Pending
- 1980-08-18 US US06/179,169 patent/US4315019A/en not_active Expired - Lifetime
- 1980-10-15 US US06/197,170 patent/US4315020A/en not_active Expired - Lifetime

Also Published As

Publication number	Publication date
FR2358890A1 (fr)	1978-02-17
FR2358890B1 (de)	1978-12-15
US4267345A (en)	1981-05-12
SU725561A3 (ru)	1980-03-30
JPS584715B2 (ja)	1983-01-27
NZ184175A (en)	1979-07-11
SU791234A3 (ru)	1980-12-23
JPS5325565A (en)	1978-03-09
GB1564268A (en)	1980-04-02
HU177039B (hu)	1981-06-28
AR219296A1 (es)	1980-08-15
AT350062B (de)	1979-05-10
GR61659B (en)	1978-12-05
US4315019A (en)	1982-02-09
JPS55127390A (en)	1980-10-02
GB1564269A (en)	1980-04-02
IL52137A (en)	1982-01-31
AU517715B2 (en)	1981-08-20
AR222022A1 (es)	1981-04-15
US4315020A (en)	1982-02-09
BE854908A (fr)	1977-11-23
PT66584B (fr)	1978-10-20
OA05668A (fr)	1981-05-31
NL169182C (nl)	1982-06-16
IL52137A0 (en)	1977-07-31
AU2537677A (en)	1978-11-30
ES459086A1 (es)	1978-04-16
ATA368277A (de)	1978-10-15
DE2723464C2 (de)	1983-08-11
DE2723464A1 (de)	1977-12-08
NL169182B (nl)	1982-01-18
PT66584A (fr)	1977-06-01
NL7705727A (nl)	1977-11-28
PH13880A (en)	1980-10-24
SE7705986L (sv)	1977-11-25

Legal Events

Date	Code	Title	Description
1983-01-31	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
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EP0213006B1 (de)	1989-01-25	2,3-Dihydrobenzofuran-Derivate, mehrere Verfahren zu ihrer Herstellung und sie enthaltende Arzneimittel
BE897566A (fr)	1983-12-16	Derives d'acides w-amines, leur preparation et utilisation ainsi que les compositions contenant ces derives.
EP0239436B1 (de)	1990-06-20	Tricyclisches Derivat, nämlich 5-(3-Chloro-6-methyl-5,5-dioxo-6,11-dihydro-dibenzo[c,f] [1,2]-thiazepin-11-yl amino)-pentansäure, Verfahren zu seiner Herstellung und dieses enthaltende Arzneimittel
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EP0376850B1 (de)	1993-03-03	Benzol-Derivate, ihre Herstellung und pharmazeutische Zusammensetzungen, die diese enthalten
CH630382A5 (fr)	1982-06-15	Pyrroloquinoxalines et leurs sels.
CA1081222A (fr)	1980-07-08	Procede de preparation de nouvelles benzazepines et leurs sels
EP0926145A1 (de)	1999-06-30	Naphthalinverbindungen, Verfahren zu ihrer Herstellung und sie enthaltende pharmazeutische Zubereitungen
CA2010529A1 (fr)	1990-08-22	Derives de la 1-arylsulfonyl 2-piperidinone, leur procede et les intermediaires de preparation, leur application comme medicaments et les compositions les renfermant
EP0105881B1 (de)	1987-12-23	Cyanguanidine, verfahren zu deren herstellung und diese enthaltende pharmazeutische zusammensetzungen
EP0067094B1 (de)	1985-10-02	Heterocyclische Derivate von Amidoxinen, ihre Herstellung und therapeutische Verwendung
FR2539415A1 (fr)	1984-07-20	Derives de la d-2 imidazoline, leur preparation et leur application en therapeutique
EP0158545B1 (de)	1987-04-22	[Alpha-(Alkylaminomethyl)-Benzylthio]-essigsäure-Derivate, Verfahren zur Herstellung und Verwendung in Therapie
EP0097546B1 (de)	1985-09-25	Benzhydrylsulfinylethylamine, Verfahren zu deren Herstellung und Verwendung in der Therapeutik
WO2000066545A1 (fr)	2000-11-09	Derives de 6-[[(aryl et heteroaryl) oxy]methyl] n aphtalene-2- carboximidamide, leur preparation et leur application en therapeutique
EP0037777B1 (de)	1983-09-28	Verfahren zur Herstellung von als Heilmittel verwendbaren Cycloalcoyl-propanol-aminen
FR2628738A1 (fr)	1989-09-22	Produits chimiques intermediaires utilisables pour la preparation de certains agents anti-histaminiques h2