IL102790A - 3-Cycloalkyl-prop-2- enamide derivatives - Google Patents

3-Cycloalkyl-prop-2- enamide derivatives

Info

Publication number: IL102790A
Authority: IL; Israel
Prior art keywords: group; formula; compound; atom; compounds
Prior art date: 1991-09-17

Application number

IL10279092A

Other languages

English (en)

Other versions

IL102790A0 (en

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.)

1991-09-17

Filing date

1992-08-11

Publication date

1996-01-31

1991-09-17 Priority claimed from GB919119874A external-priority patent/GB9119874D0/en

1992-08-11 Application filed by Roussel Uclaf filed Critical Roussel Uclaf

1993-01-31 Publication of IL102790A0 publication Critical patent/IL102790A0/xx

1996-01-31 Publication of IL102790A publication Critical patent/IL102790A/en

Links

238000000034 method Methods 0.000 claims abstract description 21
150000003839 salts Chemical class 0.000 claims abstract description 20
230000008569 process Effects 0.000 claims abstract description 16
239000003814 drug Substances 0.000 claims abstract description 11
125000005843 halogen group Chemical group 0.000 claims abstract description 10
239000000203 mixture Substances 0.000 claims abstract description 8
238000002360 preparation method Methods 0.000 claims abstract description 7
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims abstract description 3
150000001875 compounds Chemical class 0.000 claims description 74
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 34
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 30
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 12
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 11
125000004432 carbon atom Chemical group C* 0.000 claims description 11
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 8
125000000217 alkyl group Chemical group 0.000 claims description 8
229910052801 chlorine Inorganic materials 0.000 claims description 8
229910052731 fluorine Inorganic materials 0.000 claims description 8
229910052740 iodine Inorganic materials 0.000 claims description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
239000008194 pharmaceutical composition Substances 0.000 claims description 8
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 7
239000000546 pharmaceutical excipient Substances 0.000 claims description 7
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 6
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 6
125000001309 chloro group Chemical group Cl* 0.000 claims description 6
201000010099 disease Diseases 0.000 claims description 6
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 6
125000001153 fluoro group Chemical group F* 0.000 claims description 6
125000004430 oxygen atom Chemical group O* 0.000 claims description 6
239000012312 sodium hydride Substances 0.000 claims description 6
229910000104 sodium hydride Inorganic materials 0.000 claims description 6
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
125000002560 nitrile group Chemical group 0.000 claims description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
238000006243 chemical reaction Methods 0.000 claims description 4
208000037976 chronic inflammation Diseases 0.000 claims description 4
208000037893 chronic inflammatory disorder Diseases 0.000 claims description 4
230000001404 mediated effect Effects 0.000 claims description 4
206010039073 rheumatoid arthritis Diseases 0.000 claims description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
241001465754 Metazoa Species 0.000 claims description 3
239000004480 active ingredient Substances 0.000 claims description 3
239000003054 catalyst Substances 0.000 claims description 3
125000000753 cycloalkyl group Chemical group 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 3
239000001257 hydrogen Substances 0.000 claims description 3
229910052742 iron Inorganic materials 0.000 claims description 3
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 claims description 3
208000023275 Autoimmune disease Diseases 0.000 claims description 2
208000009329 Graft vs Host Disease Diseases 0.000 claims description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
239000003937 drug carrier Substances 0.000 claims description 2
125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
229910052760 oxygen Inorganic materials 0.000 claims description 2
239000001301 oxygen Substances 0.000 claims description 2
230000009467 reduction Effects 0.000 claims description 2
238000002054 transplantation Methods 0.000 claims description 2
238000002560 therapeutic procedure Methods 0.000 claims 1
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 1
229910052736 halogen Inorganic materials 0.000 abstract 2
125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 1
125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 abstract 1
150000002367 halogens Chemical class 0.000 abstract 1
-1 2-cyano 3-cyclopropyl 3-hydroxy (4-phenoxyphenyl) Chemical group 0.000 description 25
238000004458 analytical method Methods 0.000 description 21
TWSCVZUCNWUBGX-UHFFFAOYSA-N 3-hydroxyprop-2-enamide Chemical compound NC(=O)C=CO TWSCVZUCNWUBGX-UHFFFAOYSA-N 0.000 description 14
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
239000000725 suspension Substances 0.000 description 11
239000000243 solution Substances 0.000 description 10
239000000460 chlorine Substances 0.000 description 9
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
239000011780 sodium chloride Substances 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 7
238000002347 injection Methods 0.000 description 7
239000007924 injection Substances 0.000 description 7
239000007787 solid Substances 0.000 description 7
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
206010030113 Oedema Diseases 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
210000002683 foot Anatomy 0.000 description 6
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
101150041968 CDC13 gene Proteins 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 5
241000700159 Rattus Species 0.000 description 4
235000019439 ethyl acetate Nutrition 0.000 description 4
108010077055 methylated bovine serum albumin Proteins 0.000 description 4
CCHDJLYXBXITGQ-UHFFFAOYSA-N 2-cyano-3-cyclopropyl-3-hydroxyprop-2-enamide Chemical compound NC(=O)C(C#N)=C(O)C1CC1 CCHDJLYXBXITGQ-UHFFFAOYSA-N 0.000 description 3
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
229920002472 Starch Polymers 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000012267 brine Substances 0.000 description 3
229960001760 dimethyl sulfoxide Drugs 0.000 description 3
229940093499 ethyl acetate Drugs 0.000 description 3
210000000548 hind-foot Anatomy 0.000 description 3
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
239000008101 lactose Substances 0.000 description 3
235000019359 magnesium stearate Nutrition 0.000 description 3
229910052943 magnesium sulfate Inorganic materials 0.000 description 3
230000004044 response Effects 0.000 description 3
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
239000008107 starch Substances 0.000 description 3
235000019698 starch Nutrition 0.000 description 3
239000000454 talc Substances 0.000 description 3
229910052623 talc Inorganic materials 0.000 description 3
208000027930 type IV hypersensitivity disease Diseases 0.000 description 3
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
125000004938 5-pyridyl group Chemical group N1=CC=CC(=C1)* 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
206010070834 Sensitisation Diseases 0.000 description 2
239000002671 adjuvant Substances 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
239000000427 antigen Substances 0.000 description 2
102000036639 antigens Human genes 0.000 description 2
108091007433 antigens Proteins 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
239000002775 capsule Substances 0.000 description 2
239000000679 carrageenan Substances 0.000 description 2
235000010418 carrageenan Nutrition 0.000 description 2
229920001525 carrageenan Polymers 0.000 description 2
229940113118 carrageenan Drugs 0.000 description 2
DGJMPUGMZIKDRO-UHFFFAOYSA-N cyanoacetamide Chemical compound NC(=O)CC#N DGJMPUGMZIKDRO-UHFFFAOYSA-N 0.000 description 2
MLIREBYILWEBDM-UHFFFAOYSA-N cyanoacetic acid Chemical compound OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 description 2
239000003480 eluent Substances 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
238000003818 flash chromatography Methods 0.000 description 2
239000011737 fluorine Substances 0.000 description 2
238000009472 formulation Methods 0.000 description 2
150000007529 inorganic bases Chemical class 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
239000013642 negative control Substances 0.000 description 2
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
239000000843 powder Substances 0.000 description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
238000003756 stirring Methods 0.000 description 2
235000012222 talc Nutrition 0.000 description 2
239000003981 vehicle Substances 0.000 description 2
UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 2
GDEZSMXXDMVYHT-UHFFFAOYSA-N 1-(4-chlorophenoxy)-4-nitrobenzene Chemical compound C1=CC([N+](=O)[O-])=CC=C1OC1=CC=C(Cl)C=C1 GDEZSMXXDMVYHT-UHFFFAOYSA-N 0.000 description 1
WFQDTOYDVUWQMS-UHFFFAOYSA-N 1-fluoro-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(F)C=C1 WFQDTOYDVUWQMS-UHFFFAOYSA-N 0.000 description 1
BAZVFQBTJPBRTJ-UHFFFAOYSA-N 2-chloro-5-nitropyridine Chemical compound [O-][N+](=O)C1=CC=C(Cl)N=C1 BAZVFQBTJPBRTJ-UHFFFAOYSA-N 0.000 description 1
ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical compound OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 description 1
WGLBHCBJDGKRQG-UHFFFAOYSA-N 4-(4-iodophenoxy)aniline Chemical compound C1=CC(N)=CC=C1OC1=CC=C(I)C=C1 WGLBHCBJDGKRQG-UHFFFAOYSA-N 0.000 description 1
WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 description 1
244000215068 Acacia senegal Species 0.000 description 1
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
239000001828 Gelatine Substances 0.000 description 1
229920000084 Gum arabic Polymers 0.000 description 1
241000699666 Mus <mouse, genus> Species 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
241000187479 Mycobacterium tuberculosis Species 0.000 description 1
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
239000000205 acacia gum Substances 0.000 description 1
235000010489 acacia gum Nutrition 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000004913 activation Effects 0.000 description 1
230000003110 anti-inflammatory effect Effects 0.000 description 1
230000000890 antigenic effect Effects 0.000 description 1
239000012223 aqueous fraction Substances 0.000 description 1
239000008135 aqueous vehicle Substances 0.000 description 1
238000010876 biochemical test Methods 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
229940110456 cocoa butter Drugs 0.000 description 1
235000019868 cocoa butter Nutrition 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
239000013078 crystal Substances 0.000 description 1
125000004093 cyano group Chemical group *C#N 0.000 description 1
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
ZOOSILUVXHVRJE-UHFFFAOYSA-N cyclopropanecarbonyl chloride Chemical compound ClC(=O)C1CC1 ZOOSILUVXHVRJE-UHFFFAOYSA-N 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
239000008187 granular material Substances 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
239000005457 ice water Substances 0.000 description 1
210000002865 immune cell Anatomy 0.000 description 1
230000001900 immune effect Effects 0.000 description 1
239000012535 impurity Substances 0.000 description 1
230000028709 inflammatory response Effects 0.000 description 1
239000011630 iodine Substances 0.000 description 1
239000002973 irritant agent Substances 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
238000002955 isolation Methods 0.000 description 1
239000007788 liquid Substances 0.000 description 1
125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000002687 nonaqueous vehicle Substances 0.000 description 1
125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
239000012188 paraffin wax Substances 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
229910003446 platinum oxide Inorganic materials 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
238000010254 subcutaneous injection Methods 0.000 description 1
239000007929 subcutaneous injection Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000000829 suppository 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
235000013311 vegetables Nutrition 0.000 description 1
238000009736 wetting Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/72—Nitrogen atoms
- C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/31—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing rings other than six-membered aromatic rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/26—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C317/32—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C317/34—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having sulfone or sulfoxide groups and amino groups bound to carbon atoms of six-membered aromatic rings being part of the same non-condensed ring or of a condensed ring system containing that ring
- C07C317/38—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having sulfone or sulfoxide groups and amino groups bound to carbon atoms of six-membered aromatic rings being part of the same non-condensed ring or of a condensed ring system containing that ring with the nitrogen atom of at least one amino group being part of any of the groups, X being a hetero atom, Y being any atom, e.g. N-acylaminosulfones
- C07C317/40—Y being a hydrogen or a carbon atom
- 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
- C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C323/39—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton at least one of the nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom
- C07C323/40—Y being a hydrogen or a carbon atom
- C07C323/41—Y being a hydrogen or an acyclic carbon atom
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
- C07D317/58—Radicals substituted by nitrogen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Veterinary Medicine (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Public Health (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Immunology (AREA)
Pain & Pain Management (AREA)
Rheumatology (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Medicinal Preparation (AREA)
Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
Pyridine Compounds (AREA)
Detergent Compositions (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)

IL10279092A 1991-09-17 1992-08-11 3-Cycloalkyl-prop-2- enamide derivatives IL102790A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB919119874A GB9119874D0 (en)	1991-09-17	1991-09-17	3-cylopropyl-prop-2-enamide derivatives
GB929213972A GB9213972D0 (en)	1991-09-17	1992-07-01	3-cycloalkyl-prop-2-enamide derivatives

Publications (2)

Publication Number	Publication Date
IL102790A0 IL102790A0 (en)	1993-01-31
IL102790A true IL102790A (en)	1996-01-31

Family

ID=26299550

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL10279092A IL102790A (en)	1991-09-17	1992-08-11	3-Cycloalkyl-prop-2- enamide derivatives

Country Status (19)

Country	Link
US (2)	US5312830A (es)
EP (1)	EP0533573B1 (es)
JP (1)	JP3145803B2 (es)
CN (1)	CN1028863C (es)
AT (1)	ATE145893T1 (es)
AU (1)	AU649881B2 (es)
BR (1)	BR9203643A (es)
CA (1)	CA2078466C (es)
CZ (1)	CZ281674B6 (es)
DE (1)	DE69215625T2 (es)
DK (1)	DK0533573T3 (es)
ES (1)	ES2095434T3 (es)
FI (1)	FI111248B (es)
GR (1)	GR3022423T3 (es)
HU (1)	HU210164B (es)
IL (1)	IL102790A (es)
MX (1)	MX9205246A (es)
NO (1)	NO178299C (es)
NZ (1)	NZ244329A (es)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB9300083D0 (en) *	1993-01-05	1993-03-03	Roussel Lab Ltd	Chemical compounds
GB9313365D0 (en) *	1993-06-29	1993-08-11	Roussel Lab Ltd	Chemical compounds
GB9520092D0 (en) *	1995-10-02	1995-12-06	Hoechst Roussel Ltd	Chemical compounds
EP3071199A2 (en)	2013-11-22	2016-09-28	Genzyme Corporation	Novel methods for treating neurodegenerative diseases
MX2019009200A (es) *	2017-02-03	2019-10-21	Univ California	Composiciones y métodos para inhibir el reticulón 4.
WO2018144869A1 (en) *	2017-02-03	2018-08-09	The Regents Of The University Of California	Compositons and methods for modulating uba5
GB2588707B8 (en) *	2019-08-21	2025-08-06	William Page Roland	Improved containers

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NL186239B (nl) *	1975-06-05		Hoechst Ag	Werkwijze voor de bereiding van een geneesmiddel met antiflogistische en/of analgetische werking, alsmede werkwijze voor de bereiding van een 2-hydroxyethylideencyaanazijnzuuranilide geschikt voor toepassing bij deze werkwijze.
DE2555789A1 (de) *	1975-12-11	1977-07-07	Hoechst Ag	Neue cyanessigsaeureanilid-derivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende mittel
US4414395A (en) *	1980-03-13	1983-11-08	Ciba-Geigy Corporation	Process for the manufacture of hydrazono-isoindolines
US4435407A (en) *	1982-01-07	1984-03-06	Ciba-Geigy Corporation	Certain substituted β-oxo-α-carbamoylpyrrolepropionitriles
GB8619432D0 (en) *	1986-08-08	1986-09-17	Lilly Industries Ltd	Pharmaceutical compounds
US4888357A (en) *	1988-01-26	1989-12-19	Bristol-Myers Company	Antiarthritic β-cycloalkyl-β-oxopropionitriles
DE69002792T2 (de) *	1989-05-09	1993-12-09	Sds Biotech Corp	Crotonsäureamidderivate und sie enthaltende Insektizide.
US5034410A (en) *	1989-10-11	1991-07-23	Syntex (U.S.A.) Inc.	Anthelmintically active benzenepropanamide derivatives
IL99811A (en) *	1990-10-30	1996-03-31	Roussel Uclaf	3-cycloalkyl-propanamides their tautomer forms and their salts preparation process and compositions containing them

1992
- 1992-08-11 IL IL10279092A patent/IL102790A/en not_active IP Right Cessation
- 1992-08-27 CZ CS922653A patent/CZ281674B6/cs not_active IP Right Cessation
- 1992-09-14 NZ NZ244329A patent/NZ244329A/en not_active IP Right Cessation
- 1992-09-14 US US07/944,830 patent/US5312830A/en not_active Expired - Lifetime
- 1992-09-15 MX MX9205246A patent/MX9205246A/es unknown
- 1992-09-15 HU HU9202942A patent/HU210164B/hu unknown
- 1992-09-16 NO NO923603A patent/NO178299C/no not_active IP Right Cessation
- 1992-09-16 JP JP27072992A patent/JP3145803B2/ja not_active Expired - Lifetime
- 1992-09-16 AU AU24516/92A patent/AU649881B2/en not_active Expired
- 1992-09-16 FI FI924145A patent/FI111248B/fi not_active IP Right Cessation
- 1992-09-17 DK DK92402554.7T patent/DK0533573T3/da active
- 1992-09-17 EP EP92402554A patent/EP0533573B1/fr not_active Expired - Lifetime
- 1992-09-17 BR BR929203643A patent/BR9203643A/pt not_active Application Discontinuation
- 1992-09-17 CN CN92110722A patent/CN1028863C/zh not_active Expired - Lifetime
- 1992-09-17 ES ES92402554T patent/ES2095434T3/es not_active Expired - Lifetime
- 1992-09-17 DE DE69215625T patent/DE69215625T2/de not_active Expired - Lifetime
- 1992-09-17 CA CA002078466A patent/CA2078466C/fr not_active Expired - Lifetime
- 1992-09-17 AT AT92402554T patent/ATE145893T1/de active
1994
- 1994-01-21 US US08/184,566 patent/US5389652A/en not_active Expired - Lifetime
1997
- 1997-01-30 GR GR960401134T patent/GR3022423T3/el unknown

Also Published As

Publication number	Publication date
AU649881B2 (en)	1994-06-02
EP0533573A3 (fr)	1993-05-19
HUT62555A (en)	1993-05-28
JP3145803B2 (ja)	2001-03-12
ES2095434T3 (es)	1997-02-16
DE69215625T2 (de)	1997-04-17
NZ244329A (en)	1994-09-27
JPH05230008A (ja)	1993-09-07
AU2451692A (en)	1993-03-18
DE69215625D1 (de)	1997-01-16
HU9202942D0 (en)	1992-11-30
CN1028863C (zh)	1995-06-14
CZ265392A3 (en)	1993-06-16
CN1070637A (zh)	1993-04-07
NO923603L (no)	1993-03-18
DK0533573T3 (da)	1997-04-07
CA2078466A1 (fr)	1993-03-18
CZ281674B6 (cs)	1996-12-11
ATE145893T1 (de)	1996-12-15
FI924145L (fi)	1993-03-18
NO178299B (no)	1995-11-20
CA2078466C (fr)	2003-04-15
FI111248B (fi)	2003-06-30
HU210164B (en)	1995-02-28
MX9205246A (es)	1994-06-30
EP0533573A2 (fr)	1993-03-24
US5312830A (en)	1994-05-17
NO923603D0 (no)	1992-09-16
NO178299C (no)	1996-02-28
EP0533573B1 (fr)	1996-12-04
FI924145A0 (fi)	1992-09-16
US5389652A (en)	1995-02-14
IL102790A0 (en)	1993-01-31
BR9203643A (pt)	1993-04-13
GR3022423T3 (en)	1997-04-30

Legal Events

Date	Code	Title
1996-07-23	FF	Patent granted
1999-01-26	KB	Patent renewed
2000-06-01	HCE	Change of name and address of proprietor(s)
2002-09-12	KB	Patent renewed
2003-01-12	HCA	Change of name of proprietor(s) after amalgamation
2006-10-04	KB	Patent renewed
2010-11-30	KB	Patent renewed
2013-03-24	EXP	Patent expired

Publication	Publication Date	Title
EP3329775B1 (en)	2021-04-21	Processes for the synthesis of diarylthiohydantoin and diarylhydantoin compounds
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NZ507639A (en)	2004-01-30	Imidazo pyridine dervatives which inhibit gastric acid secretion
IL102790A (en)	1996-01-31	3-Cycloalkyl-prop-2- enamide derivatives
US5476866A (en)	1995-12-19	Isoxazoles
JP3642797B2 (ja)	2005-04-27	フェニルカルボキサミドイソオキサゾールの新誘導体及びそれらの塩類、それらの製造法及びこの製造法の新規な中間体、それらの薬剤としての用途並びにそれらを含有する製薬組成物
US6214882B1 (en)	2001-04-10	Benzenesulphonamide derivatives, preparation thereof and therapeutical uses thereof
FR2471376A1 (fr)	1981-06-19	Derives de thioethylamide, utiles comme bloqueurs d'histamine h2
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