CH617685A5 - - Google Patents

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Publication number: CH617685A5
Authority: CH; Switzerland
Prior art keywords: radical; phenyl; formula; product; nitro
Prior art date: 1975-10-15

Application number

CH1303476A

Other languages

English (en)

French (fr)

Inventor

Claude Bonne

Jacques Perronnet

Andre Teche

Original Assignee

Roussel Uclaf

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.)

1975-10-15

Filing date

1976-10-14

Publication date

1980-06-13

1976-10-14 Application filed by Roussel Uclaf filed Critical Roussel Uclaf

1980-06-13 Publication of CH617685A5 publication Critical patent/CH617685A5/fr

Links

-1 alkyl radical Chemical class 0.000 claims description 22
150000005063 oxadiazines Chemical class 0.000 claims description 21
238000000034 method Methods 0.000 claims description 20
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 14
125000004432 carbon atom Chemical group C* 0.000 claims description 13
BLNWTAHYTCHDJH-UHFFFAOYSA-O hydroxy(oxo)azanium Chemical compound O[NH+]=O BLNWTAHYTCHDJH-UHFFFAOYSA-O 0.000 claims description 12
WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical compound F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 claims description 10
OUGJPFAQCLLRPU-UHFFFAOYSA-N 1,2,4-oxadiazinan-3-one Chemical compound O=C1NCCON1 OUGJPFAQCLLRPU-UHFFFAOYSA-N 0.000 claims description 9
125000001309 chloro group Chemical group Cl* 0.000 claims description 9
238000007327 hydrogenolysis reaction Methods 0.000 claims description 9
238000002360 preparation method Methods 0.000 claims description 9
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
150000001875 compounds Chemical class 0.000 claims description 7
125000005843 halogen group Chemical group 0.000 claims description 7
PIEXCQIOSMOEOU-UHFFFAOYSA-N 1-bromo-3-chloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Br)C(=O)N(Cl)C1=O PIEXCQIOSMOEOU-UHFFFAOYSA-N 0.000 claims description 6
SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims description 6
239000003054 catalyst Substances 0.000 claims description 6
229910052801 chlorine Inorganic materials 0.000 claims description 5
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 3
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
150000003254 radicals Chemical class 0.000 claims description 3
QMEQBOSUJUOXMX-UHFFFAOYSA-N 2h-oxadiazine Chemical compound N1OC=CC=N1 QMEQBOSUJUOXMX-UHFFFAOYSA-N 0.000 claims description 2
125000004414 alkyl thio group Chemical group 0.000 claims 1
239000000047 product Substances 0.000 description 71
239000000203 mixture Substances 0.000 description 24
230000005764 inhibitory process Effects 0.000 description 16
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
210000000056 organ Anatomy 0.000 description 11
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
238000004458 analytical method Methods 0.000 description 9
230000002280 anti-androgenic effect Effects 0.000 description 8
238000010348 incorporation Methods 0.000 description 8
238000011282 treatment Methods 0.000 description 8
NVKAWKQGWWIWPM-ABEVXSGRSA-N 17-β-hydroxy-5-α-Androstan-3-one Chemical compound C1C(=O)CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CC[C@H]21 NVKAWKQGWWIWPM-ABEVXSGRSA-N 0.000 description 7
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 7
229960003473 androstanolone Drugs 0.000 description 7
230000000694 effects Effects 0.000 description 7
239000000243 solution Substances 0.000 description 7
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
PDMMFKSKQVNJMI-BLQWBTBKSA-N Testosterone propionate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](OC(=O)CC)[C@@]1(C)CC2 PDMMFKSKQVNJMI-BLQWBTBKSA-N 0.000 description 6
239000000460 chlorine Substances 0.000 description 6
229960001712 testosterone propionate Drugs 0.000 description 6
241001465754 Metazoa Species 0.000 description 5
IQFYYKKMVGJFEH-XLPZGREQSA-N Thymidine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](O)C1 IQFYYKKMVGJFEH-XLPZGREQSA-N 0.000 description 5
229910000027 potassium carbonate Inorganic materials 0.000 description 5
210000002307 prostate Anatomy 0.000 description 5
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 4
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
102000053602 DNA Human genes 0.000 description 4
108020004414 DNA Proteins 0.000 description 4
238000004587 chromatography analysis Methods 0.000 description 4
RGZRSLKIOCHTSI-UHFFFAOYSA-N hydron;n-methylhydroxylamine;chloride Chemical compound Cl.CNO RGZRSLKIOCHTSI-UHFFFAOYSA-N 0.000 description 4
102000002260 Alkaline Phosphatase Human genes 0.000 description 3
108020004774 Alkaline Phosphatase Proteins 0.000 description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
241000699800 Cricetinae Species 0.000 description 3
LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 3
241000700159 Rattus Species 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
239000003098 androgen Substances 0.000 description 3
TXHIDIHEXDFONW-UHFFFAOYSA-N benzene;propan-2-one Chemical compound CC(C)=O.C1=CC=CC=C1 TXHIDIHEXDFONW-UHFFFAOYSA-N 0.000 description 3
238000005119 centrifugation Methods 0.000 description 3
229940088597 hormone Drugs 0.000 description 3
239000005556 hormone Substances 0.000 description 3
239000012948 isocyanate Substances 0.000 description 3
150000002513 isocyanates Chemical class 0.000 description 3
238000010992 reflux Methods 0.000 description 3
238000012360 testing method Methods 0.000 description 3
229960003604 testosterone Drugs 0.000 description 3
VBUQDIPNGMAETH-UHFFFAOYSA-N 1-hydroxy-1-methyl-3-[4-methyl-3-(trifluoromethyl)thiophen-2-yl]urea Chemical compound FC(C1=C(SC=C1C)NC(=O)N(O)C)(F)F VBUQDIPNGMAETH-UHFFFAOYSA-N 0.000 description 2
MZXJCGSBGWEIRJ-UHFFFAOYSA-N 2-benzyl-4-(3,4-dichlorophenyl)-1,2,4-oxadiazinan-3-one Chemical compound C1=C(Cl)C(Cl)=CC=C1N1C(=O)N(CC=2C=CC=CC=2)OCC1 MZXJCGSBGWEIRJ-UHFFFAOYSA-N 0.000 description 2
YHVNZBIWANMOMU-UHFFFAOYSA-N 3-(3,4-dichlorophenyl)-1-hydroxy-1-pentylurea Chemical compound CCCCCN(O)C(=O)NC1=CC=C(Cl)C(Cl)=C1 YHVNZBIWANMOMU-UHFFFAOYSA-N 0.000 description 2
HSKUNUIBPSUGRD-UHFFFAOYSA-N 3-(3,5-dichlorophenyl)-1-hydroxy-1-methylurea Chemical compound CN(O)C(=O)NC1=CC(Cl)=CC(Cl)=C1 HSKUNUIBPSUGRD-UHFFFAOYSA-N 0.000 description 2
WOZFGHSLOHGHAK-UHFFFAOYSA-N 3-[4-chloro-3-(trifluoromethyl)phenyl]-1-hydroxy-1-methylurea Chemical compound CN(O)C(=O)NC1=CC=C(Cl)C(C(F)(F)F)=C1 WOZFGHSLOHGHAK-UHFFFAOYSA-N 0.000 description 2
NJVFXWJWUKLIIO-UHFFFAOYSA-N 4-isocyanato-1-methylsulfanyl-2-(trifluoromethyl)benzene Chemical compound CSC1=CC=C(N=C=O)C=C1C(F)(F)F NJVFXWJWUKLIIO-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
241000699673 Mesocricetus auratus Species 0.000 description 2
JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
MUMGGOZAMZWBJJ-DYKIIFRCSA-N Testostosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 MUMGGOZAMZWBJJ-DYKIIFRCSA-N 0.000 description 2
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
239000000051 antiandrogen Substances 0.000 description 2
TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
229940079593 drug Drugs 0.000 description 2
239000003814 drug Substances 0.000 description 2
238000005755 formation reaction Methods 0.000 description 2
239000012634 fragment Substances 0.000 description 2
229910052736 halogen Inorganic materials 0.000 description 2
150000002367 halogens Chemical class 0.000 description 2
239000005457 ice water Substances 0.000 description 2
239000007924 injection Substances 0.000 description 2
238000002347 injection Methods 0.000 description 2
239000006210 lotion Substances 0.000 description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
239000002674 ointment Substances 0.000 description 2
PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical group Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
239000002798 polar solvent Substances 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 2
239000000126 substance Substances 0.000 description 2
229940104230 thymidine Drugs 0.000 description 2
238000005303 weighing Methods 0.000 description 2
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
XEFUJGURFLOFAN-UHFFFAOYSA-N 1,3-dichloro-5-isocyanatobenzene Chemical compound ClC1=CC(Cl)=CC(N=C=O)=C1 XEFUJGURFLOFAN-UHFFFAOYSA-N 0.000 description 1
MTHOFZLXPGDEKR-UHFFFAOYSA-N 1-benzyl-3-(3,4-dichlorophenyl)-1-hydroxyurea Chemical compound C=1C=C(Cl)C(Cl)=CC=1NC(=O)N(O)CC1=CC=CC=C1 MTHOFZLXPGDEKR-UHFFFAOYSA-N 0.000 description 1
NBJZEUQTGLSUOB-UHFFFAOYSA-N 1-chloro-4-isocyanato-2-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC(N=C=O)=CC=C1Cl NBJZEUQTGLSUOB-UHFFFAOYSA-N 0.000 description 1
HQROXDLWVGFPDE-UHFFFAOYSA-N 1-chloro-4-nitro-2-(trifluoromethyl)benzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C(C(F)(F)F)=C1 HQROXDLWVGFPDE-UHFFFAOYSA-N 0.000 description 1
SXQIEPLNJQLXPK-UHFFFAOYSA-N 1-hydroxy-1-methyl-3-(3-nitrophenyl)urea Chemical compound CN(O)C(=O)NC1=CC=CC([N+]([O-])=O)=C1 SXQIEPLNJQLXPK-UHFFFAOYSA-N 0.000 description 1
MTFFANYLEXKMTD-UHFFFAOYSA-N 1-hydroxy-1-phenylurea Chemical compound NC(=O)N(O)C1=CC=CC=C1 MTFFANYLEXKMTD-UHFFFAOYSA-N 0.000 description 1
BKAXBXQLSZSMLB-UHFFFAOYSA-N 1-methylsulfanyl-4-nitro-2-(trifluoromethyl)benzene Chemical compound CSC1=CC=C([N+]([O-])=O)C=C1C(F)(F)F BKAXBXQLSZSMLB-UHFFFAOYSA-N 0.000 description 1
SQAORNVRAYTOMS-UHFFFAOYSA-N 2-methyl-4-[4-nitro-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazinan-3-one Chemical compound O=C1N(C)OCCN1C1=CC=C([N+]([O-])=O)C(C(F)(F)F)=C1 SQAORNVRAYTOMS-UHFFFAOYSA-N 0.000 description 1
125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 1
MFUVCHZWGSJKEQ-UHFFFAOYSA-N 3,4-dichlorphenylisocyanate Chemical compound ClC1=CC=C(N=C=O)C=C1Cl MFUVCHZWGSJKEQ-UHFFFAOYSA-N 0.000 description 1
XTZKSJGASNPSNO-UHFFFAOYSA-N 3-(2,4-dichlorophenyl)-1-hydroxy-1-methylurea Chemical compound CN(O)C(=O)NC1=CC=C(Cl)C=C1Cl XTZKSJGASNPSNO-UHFFFAOYSA-N 0.000 description 1
KSTVNIMAJMFMKA-UHFFFAOYSA-N 4-(3,4-dichlorophenyl)-1,2,4-oxadiazinan-3-one Chemical compound C1=C(Cl)C(Cl)=CC=C1N1C(=O)NOCC1 KSTVNIMAJMFMKA-UHFFFAOYSA-N 0.000 description 1
NLDKQOJJXCNRAJ-UHFFFAOYSA-N 4-(3,4-dichlorophenyl)-2-ethyl-1,2,4-oxadiazinan-3-one Chemical compound O=C1N(CC)OCCN1C1=CC=C(Cl)C(Cl)=C1 NLDKQOJJXCNRAJ-UHFFFAOYSA-N 0.000 description 1
FTUOLIYZLWDBDH-UHFFFAOYSA-N 4-(3,4-dichlorophenyl)-2-methyl-1,2,4-oxadiazinan-3-one Chemical compound O=C1N(C)OCCN1C1=CC=C(Cl)C(Cl)=C1 FTUOLIYZLWDBDH-UHFFFAOYSA-N 0.000 description 1
UACCUJJOQRTDIV-UHFFFAOYSA-N 4-(3,4-dichlorophenyl)-2-pentyl-1,2,4-oxadiazinan-3-one Chemical compound O=C1N(CCCCC)OCCN1C1=CC=C(Cl)C(Cl)=C1 UACCUJJOQRTDIV-UHFFFAOYSA-N 0.000 description 1
HOARYSVZNCKNAG-UHFFFAOYSA-N 4-(4-chlorophenyl)-2-methyl-1,2,4-oxadiazinan-3-one Chemical compound O=C1N(C)OCCN1C1=CC=C(Cl)C=C1 HOARYSVZNCKNAG-UHFFFAOYSA-N 0.000 description 1
VITGUQLYTYJRTD-UHFFFAOYSA-N 4-[4-chloro-3-(trifluoromethyl)phenyl]-2-methyl-1,2,4-oxadiazinan-3-one Chemical compound O=C1N(C)OCCN1C1=CC=C(Cl)C(C(F)(F)F)=C1 VITGUQLYTYJRTD-UHFFFAOYSA-N 0.000 description 1
MBBRGNWOSWJCGG-UHFFFAOYSA-N 4-methylsulfanyl-3-(trifluoromethyl)aniline Chemical compound CSC1=CC=C(N)C=C1C(F)(F)F MBBRGNWOSWJCGG-UHFFFAOYSA-N 0.000 description 1
208000002874 Acne Vulgaris Diseases 0.000 description 1
241000894006 Bacteria Species 0.000 description 1
DWRXFEITVBNRMK-UHFFFAOYSA-N Beta-D-1-Arabinofuranosylthymine Natural products O=C1NC(=O)C(C)=CN1C1C(O)C(O)C(CO)O1 DWRXFEITVBNRMK-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
229910001018 Cast iron Inorganic materials 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
NOTFZGFABLVTIG-UHFFFAOYSA-N Cyclohexylethyl acetate Chemical compound CC(=O)OCCC1CCCCC1 NOTFZGFABLVTIG-UHFFFAOYSA-N 0.000 description 1
241000233866 Fungi Species 0.000 description 1
206010020112 Hirsutism Diseases 0.000 description 1
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
206010062767 Hypophysitis 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
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
206010039792 Seborrhoea Diseases 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
206010000496 acne Diseases 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
150000001447 alkali salts Chemical class 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
229940030486 androgens Drugs 0.000 description 1
150000001448 anilines Chemical class 0.000 description 1
230000008485 antagonism Effects 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000008135 aqueous vehicle Substances 0.000 description 1
IQFYYKKMVGJFEH-UHFFFAOYSA-N beta-L-thymidine Natural products O=C1NC(=O)C(C)=CN1C1OC(CO)C(O)C1 IQFYYKKMVGJFEH-UHFFFAOYSA-N 0.000 description 1
239000003139 biocide Substances 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000004202 carbamide Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
229910002091 carbon monoxide Inorganic materials 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
239000002537 cosmetic Substances 0.000 description 1
239000006071 cream Substances 0.000 description 1
239000012043 crude product Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
238000005520 cutting process Methods 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
238000011161 development Methods 0.000 description 1
WBKFWQBXFREOFH-UHFFFAOYSA-N dichloromethane;ethyl acetate Chemical compound ClCCl.CCOC(C)=O WBKFWQBXFREOFH-UHFFFAOYSA-N 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
230000001747 exhibiting effect Effects 0.000 description 1
239000012467 final product Substances 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
229910052595 hematite Inorganic materials 0.000 description 1
239000011019 hematite Substances 0.000 description 1
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
239000008235 industrial water Substances 0.000 description 1
239000007927 intramuscular injection Substances 0.000 description 1
238000010255 intramuscular injection Methods 0.000 description 1
239000007928 intraperitoneal injection Substances 0.000 description 1
LIKBJVNGSGBSGK-UHFFFAOYSA-N iron(3+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Fe+3].[Fe+3] LIKBJVNGSGBSGK-UHFFFAOYSA-N 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000000644 isotonic solution Substances 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
239000000463 material Substances 0.000 description 1
238000005259 measurement Methods 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
LVCDXCQFSONNDO-UHFFFAOYSA-N n-benzylhydroxylamine Chemical compound ONCC1=CC=CC=C1 LVCDXCQFSONNDO-UHFFFAOYSA-N 0.000 description 1
XEZLAJRZQNKEOJ-UHFFFAOYSA-N n-pentylhydroxylamine Chemical compound CCCCCNO XEZLAJRZQNKEOJ-UHFFFAOYSA-N 0.000 description 1
239000003921 oil Substances 0.000 description 1
235000019198 oils Nutrition 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
239000008188 pellet Substances 0.000 description 1
229940056360 penicillin g Drugs 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
230000002093 peripheral effect Effects 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
210000003635 pituitary gland Anatomy 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000000700 radioactive tracer Substances 0.000 description 1
238000011084 recovery Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
208000008742 seborrheic dermatitis Diseases 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000012453 sprague-dawley rat model Methods 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
238000003756 stirring Methods 0.000 description 1
229960005322 streptomycin Drugs 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
125000001424 substituent group Chemical class 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000001302 tertiary amino group Chemical group 0.000 description 1
210000001519 tissue Anatomy 0.000 description 1
238000011200 topical administration Methods 0.000 description 1
YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D273/00—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00
- C07D273/02—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00 having two nitrogen atoms and only one oxygen atom
- C07D273/04—Six-membered rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/64—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups singly-bound to oxygen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (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)
Cosmetics (AREA)
Electrodes Of Semiconductors (AREA)

CH1303476A 1975-10-15 1976-10-14 CH617685A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
FR7531566A FR2327788A1 (fr)	1975-10-15	1975-10-15	Medicaments nouveaux derives de la 4-phenyl 5,6-dihydro 1,2,4-oxadiazine 3-one, produits nouveaux derives de la 4-phenyl 5,6-dihydro 1,2,4-oxadiazine 3-one et leur procede de preparation

Publications (1)

Publication Number	Publication Date
CH617685A5 true CH617685A5 (de)	1980-06-13

Family

ID=9161232

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1303476A CH617685A5 (de)	1975-10-15	1976-10-14

Country Status (12)

Country	Link
US (1)	US4108993A (de)
JP (2)	JPS6058727B2 (de)
BE (1)	BE847290A (de)
CA (1)	CA1086730A (de)
CH (1)	CH617685A5 (de)
DE (1)	DE2646700A1 (de)
DK (1)	DK150543C (de)
FR (1)	FR2327788A1 (de)
GB (2)	GB1563831A (de)
IE (1)	IE44037B1 (de)
LU (1)	LU76005A1 (de)
NL (1)	NL186768C (de)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2660308B1 (fr) *	1990-03-30	1992-07-17	Roussel Uclaf	Nouveaux derives soufres du 5,6-dihydro 2-methyl 4-[3-(trifluoromethyl) phenyl] 2h-1,2,4-oxadiazin-3(4h)-one, leur procede de preparation et les intermediaires de ce procede, leur application a titre d'herbicide et les compositions les renfermant.
FR2660307B1 (fr) *	1990-03-30	1994-06-03	Roussel Uclaf	Nouveaux derives du 5,6-dihydro 2-methyl 4-[3-(trifluoromethyl) phenyl] 2h-1,2,4-oxadiazin-3(4h)-one, leur procede de preparation et les intermediaires de ce procede, leur application a titre d'herbicide et les compositions les renfermant.
FR2660158A1 (fr) *	1990-03-30	1991-10-04	Roussel Uclaf	Utilisation comme herbicides de derives de la 5,6-dihydro 2-methyl 4-phenyl 2h-1,2,4-oxadiazin-3(4h)-one, nouveaux derives de celle-ci, leur procede de preparation et les intermediaires de ce procede.
US5612377A (en) *	1994-08-04	1997-03-18	Minnesota Mining And Manufacturing Company	Method of inhibiting leukotriene biosynthesis

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3238200A (en) *	1963-06-27	1966-03-01	Olin Mathieson	Oxadiazinediones
US3537839A (en) *	1966-07-02	1970-11-03	Basf Ag	Method for controlling unwanted plant growth with 1,2,4-oxadiazines
US3625968A (en) *	1967-01-12	1971-12-07	Basf Ag	Production of tetrahydro-1,2,4-oxadiazine-3,5-diones
FR2039472A5 (de) *	1969-04-03	1971-01-15	Progil
FR2097085A1 (en) *	1970-07-31	1972-03-03	Pepro	Oxadizing herbicides - for pre - or post-emergence use
US3829419A (en) *	1973-03-26	1974-08-13	Rohm & Haas	Tetrahydro-4h-1,3,5-oxadiazin-4-one

1975
- 1975-10-15 FR FR7531566A patent/FR2327788A1/fr active Granted
1976
- 1976-10-05 US US05/729,763 patent/US4108993A/en not_active Expired - Lifetime
- 1976-10-14 BE BE171522A patent/BE847290A/xx not_active IP Right Cessation
- 1976-10-14 LU LU76005A patent/LU76005A1/xx unknown
- 1976-10-14 JP JP51122355A patent/JPS6058727B2/ja not_active Expired
- 1976-10-14 DK DK462176A patent/DK150543C/da not_active IP Right Cessation
- 1976-10-14 CH CH1303476A patent/CH617685A5/fr not_active IP Right Cessation
- 1976-10-15 CA CA263,490A patent/CA1086730A/fr not_active Expired
- 1976-10-15 GB GB42880/76A patent/GB1563831A/en not_active Expired
- 1976-10-15 NL NLAANVRAGE7611412,A patent/NL186768C/xx not_active IP Right Cessation
- 1976-10-15 DE DE19762646700 patent/DE2646700A1/de active Granted
- 1976-10-15 GB GB16230/78A patent/GB1563832A/en not_active Expired
- 1976-10-15 IE IE2283/76A patent/IE44037B1/en not_active IP Right Cessation
1985
- 1985-07-02 JP JP60144084A patent/JPS6156173A/ja active Granted

Also Published As

Publication number	Publication date
DK150543B (da)	1987-03-23
DK462176A (da)	1977-04-16
IE44037B1 (en)	1981-07-29
JPS5251380A (en)	1977-04-25
JPS6156173A (ja)	1986-03-20
DE2646700A1 (de)	1977-04-21
FR2327788A1 (fr)	1977-05-13
NL186768C (nl)	1991-02-18
IE44037L (en)	1977-04-15
JPS6319513B2 (de)	1988-04-22
GB1563831A (en)	1980-04-02
CA1086730A (fr)	1980-09-30
BE847290A (fr)	1977-04-14
DE2646700C2 (de)	1987-11-19
DK150543C (da)	1987-09-28
JPS6058727B2 (ja)	1985-12-21
NL186768B (nl)	1990-09-17
FR2327788B1 (de)	1979-10-12
US4108993A (en)	1978-08-22
LU76005A1 (de)	1977-05-25
GB1563832A (en)	1980-04-02
NL7611412A (nl)	1977-04-19

Legal Events

Date	Code	Title	Description
1993-06-30	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
EP0494819B1 (de)	1996-07-10	Phenylimidazolidine, Verfahren zu deren Herstellung, deren Anwendung als Arzneimittel und diese enthaltende pharmazeutische Zusammenstellungen
CA1304093C (fr)	1992-06-23	Imidazolidines substituees par un radical hydroxymethyle et un radical phenyle substitue, leur procede de preparation, leur application comme medicaments, lescompositions pharmaceutiques les renfermant et un intermediaire pour leur preparation
EP0580459B1 (de)	2001-03-28	Substituierte Phenylimidazolidine, ihre Anwendung als Medikamente und die sie enthaltende pharmazeutische Präparate
EP0704448B1 (de)	2001-12-05	Heterocyclisch substituierte Imidazolidine, Verfahren und Zwischenprodukte zu ihrer Herstellung, ihre Verwendung als Arzneimittel und diese enthaltende pharmazeutische Zubereitungen
EP0115997B1 (de)	1987-07-22	Omega-Mercaptopropanamid-Derivate und ihre Homologe, Verfahren zu ihrer Herstellung, ihre Verwendung als Arzneimittel, diese enthaltende Zusammensetzungen und die erhaltenen Zwischenprodukte
FR2694290A1 (fr)	1994-02-04	Nouvelles phénylimidazolidines éventuellement substituées, leur procédé de préparation, leur application comme médicaments et les compositions pharmaceutiques les renfermant.
WO1995018794A1 (fr)	1995-07-13	Nouvelles phenylimidazolidines eventuellement substituees, leur procede et des intermediaires de preparation, leur application comme medicaments et les compositions pharmaceutiques les renfermant
EP0049555A1 (de)	1982-04-14	Derivate von 2-Trifluormethyl-4-hydroxy-3-chinolin-carbonsäuren und Verfahren zu ihrer Herstellung
CH649994A5 (fr)	1985-06-28	Derives du 4h-1,2,4-triazole, procedes de preparation et compositions les renfermant.
CH617685A5 (de)	1980-06-13
EP0395528B1 (de)	1995-07-05	4-Phenylmethyl-1H-indol-Derivate, Verfahren und Zwischenverbindungen zu deren Herstellung, Anwendung als Arzneimittel und diese enthaltende Zusammensetzungen
CA1091674A (fr)	1980-12-16	Derives de l'isoquinoleine, leur preparation et les compositions qui les contiennent
EP0214004B1 (de)	1993-03-31	Gegebenenfalls etherifizierte oder esterifizierte in Stellung 2 substituierte 4-OH-Chinolincarbonsäurederivate, Verfahren und Zwischenprodukte zu ihrer Herstellung, ihre Anwendung als Arzneimittel und diese enthaltende Zubereitungen
FR2530633A1 (fr)	1984-01-27	Nouveaux derives de l'acide 4-hydroxy 3-quinoleine carboxylique substitues en 2, leur preparation, leur application comme medicament, et les compositions les renfermant
EP0169755B1 (de)	1990-05-09	4-Hydroxy-3-chinolincarbonsäurederivate, 2-substituiert durch eine Stickstoff enthaltende Gruppe, ihre Herstellung, ihre Verwendung als Arzneimittel, diese enthaltende Zubereitungen und Zwischenprodukte
CA1265805A (fr)	1990-02-13	Procede de preparation de nouveaux derives du 4- phenylpropyl indole
EP0234971B1 (de)	1990-09-05	Substituierte Carbonsäureamide, ihre Herstellung und diese enthaltende pharmazeutische Zubereitungen
CA1308721C (fr)	1992-10-13	Derives de la benzimidazol-2-one, leurs sels, procede et intermediaires de preparation, application a titre de medicaments et compositions les renfermant
EP0168309B1 (de)	1988-03-09	Isoxazolochinolinonderivate, Verfahren und Zwischenprodukte zu ihrer Herstellung, Verwendung als Arzneimittel und die sie enthaltenden Zubereitungen
EP0017523B1 (de)	1982-09-01	Derivate des Dithiepinno (1,4)(2,3-c) pyrrols, ihre Herstellung und sie enthaltende Medikamente
EP0176444A1 (de)	1986-04-02	Verfahren zur Herstellung von 4H-1,2,4-Triazol-Derivaten, so erhaltene neue Triazole, ihre Verwendung als Arzneimittel und sie enthaltende pharmazeutische Zusammensetzungen
EP0209435A1 (de)	1987-01-21	Hydroxyalkoxy-4-phenylpropylindolderivate, ihre Salze, Verfahren und Zwischenprodukte zur Herstellung, Anwendung als Heilmittel und Zusammensetzungen die sie enthalten
FR2724169A1 (fr)	1996-03-08	Nouvelles phenylimidazolidines eventuellement substituees, leur procede et des intermediaires de preparation, leur application comme medicaments et les compositions pharmaceutiques les renfermant
CH617696A5 (en)	1980-06-13	Process for the preparation of new derivatives of isoindoline
FR2611712A1 (fr)	1988-09-09	Nouveaux derives n-substitues de l'alpha-mercaptomethyl benzene propanamide, leur procede de preparation, leur application a titre de medicaments et les compositions les renfermant