CH615429A5 - - Google Patents

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Info

Publication number: CH615429A5
Authority: CH; Switzerland
Prior art keywords: formula; compound; alkyl; optionally substituted; phenyl
Prior art date: 1975-05-02

Application number

CH1242678A

Other languages

English (en)

French (fr)

Inventor

William James Ross

Alec Todd

John Pomfret Verge

Original Assignee

Lilly Industries Ltd

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.)

1975-05-02

Filing date

1978-12-05

Publication date

1980-01-31

1978-12-05 Application filed by Lilly Industries Ltd filed Critical Lilly Industries Ltd

1980-01-31 Publication of CH615429A5 publication Critical patent/CH615429A5/fr

Links

150000001875 compounds Chemical class 0.000 claims description 31
125000000217 alkyl group Chemical group 0.000 claims description 23
239000001257 hydrogen Substances 0.000 claims description 16
229910052739 hydrogen Inorganic materials 0.000 claims description 16
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 15
238000006243 chemical reaction Methods 0.000 claims description 9
238000000034 method Methods 0.000 claims description 9
238000002360 preparation method Methods 0.000 claims description 8
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
125000004432 carbon atom Chemical group C* 0.000 claims description 6
125000003342 alkenyl group Chemical group 0.000 claims description 5
ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 4
230000000694 effects Effects 0.000 claims description 3
150000007978 oxazole derivatives Chemical class 0.000 claims description 3
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
208000001718 Immediate Hypersensitivity Diseases 0.000 claims description 2
206010045240 Type I hypersensitivity Diseases 0.000 claims description 2
125000004429 atom Chemical group 0.000 claims description 2
208000010216 atopic IgE responsiveness Diseases 0.000 claims description 2
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
230000004048 modification Effects 0.000 claims description 2
238000012986 modification Methods 0.000 claims description 2
206010020751 Hypersensitivity Diseases 0.000 claims 1
208000026935 allergic disease Diseases 0.000 claims 1
230000007815 allergy Effects 0.000 claims 1
230000003266 anti-allergic effect Effects 0.000 claims 1
230000003110 anti-inflammatory effect Effects 0.000 claims 1
210000003169 central nervous system Anatomy 0.000 claims 1
125000000547 substituted alkyl group Chemical group 0.000 claims 1
-1 4-methyl-amyl Chemical group 0.000 description 10
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
239000000243 solution Substances 0.000 description 7
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
150000004657 carbamic acid derivatives Chemical class 0.000 description 4
239000000203 mixture Substances 0.000 description 4
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
239000000047 product Substances 0.000 description 4
239000003826 tablet Substances 0.000 description 4
230000001225 therapeutic effect Effects 0.000 description 4
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
238000002347 injection Methods 0.000 description 3
239000007924 injection Substances 0.000 description 3
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
125000003545 alkoxy group Chemical group 0.000 description 2
208000006673 asthma Diseases 0.000 description 2
239000003085 diluting agent Substances 0.000 description 2
239000002552 dosage form Substances 0.000 description 2
LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 2
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
KFTIPZOFAAEJCO-UHFFFAOYSA-N ethyl n-butyl-n-(4-methyl-1,3-oxazol-2-yl)carbamate Chemical compound CCCCN(C(=O)OCC)C1=NC(C)=CO1 KFTIPZOFAAEJCO-UHFFFAOYSA-N 0.000 description 2
238000001914 filtration Methods 0.000 description 2
125000001188 haloalkyl group Chemical group 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
239000003921 oil Substances 0.000 description 2
235000019198 oils Nutrition 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
239000000377 silicon dioxide Substances 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
YAPQBXQYLJRXSA-UHFFFAOYSA-N theobromine Chemical compound CN1C(=O)NC(=O)C2=C1N=CN2C YAPQBXQYLJRXSA-UHFFFAOYSA-N 0.000 description 2
CUNWUEBNSZSNRX-RKGWDQTMSA-N (2r,3r,4r,5s)-hexane-1,2,3,4,5,6-hexol;(z)-octadec-9-enoic acid Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.CCCCCCCC\C=C/CCCCCCCC(O)=O.CCCCCCCC\C=C/CCCCCCCC(O)=O.CCCCCCCC\C=C/CCCCCCCC(O)=O CUNWUEBNSZSNRX-RKGWDQTMSA-N 0.000 description 1
ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 1
125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
125000006656 (C2-C4) alkenyl group Chemical group 0.000 description 1
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 1
125000006705 (C5-C7) cycloalkyl group Chemical group 0.000 description 1
DDMOUSALMHHKOS-UHFFFAOYSA-N 1,2-dichloro-1,1,2,2-tetrafluoroethane Chemical compound FC(F)(Cl)C(F)(F)Cl DDMOUSALMHHKOS-UHFFFAOYSA-N 0.000 description 1
125000001478 1-chloroethyl group Chemical group [H]C([H])([H])C([H])(Cl)* 0.000 description 1
JQCSUVJDBHJKNG-UHFFFAOYSA-N 1-methoxy-ethyl Chemical group C[CH]OC JQCSUVJDBHJKNG-UHFFFAOYSA-N 0.000 description 1
125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
VCZJVXLWQTXSPQ-UHFFFAOYSA-N 4-methyl-1,3-oxazol-2-amine Chemical compound CC1=COC(N)=N1 VCZJVXLWQTXSPQ-UHFFFAOYSA-N 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
239000005995 Aluminium silicate Substances 0.000 description 1
241000416162 Astragalus gummifer Species 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
239000004338 Dichlorodifluoromethane Substances 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
229920000084 Gum arabic Polymers 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
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
229930195725 Mannitol Natural products 0.000 description 1
229920000168 Microcrystalline cellulose Polymers 0.000 description 1
229920000881 Modified starch Polymers 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
235000019483 Peanut oil Nutrition 0.000 description 1
229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
239000004147 Sorbitan trioleate Substances 0.000 description 1
PRXRUNOAOLTIEF-ADSICKODSA-N Sorbitan trioleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](OC(=O)CCCCCCC\C=C/CCCCCCCC)[C@H]1OC[C@H](O)[C@H]1OC(=O)CCCCCCC\C=C/CCCCCCCC PRXRUNOAOLTIEF-ADSICKODSA-N 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
208000005279 Status Asthmaticus Diseases 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
229930006000 Sucrose Natural products 0.000 description 1
229920001615 Tragacanth Polymers 0.000 description 1
235000010489 acacia gum Nutrition 0.000 description 1
239000000205 acacia gum Substances 0.000 description 1
125000004423 acyloxy group Chemical group 0.000 description 1
239000000443 aerosol Substances 0.000 description 1
235000010443 alginic acid Nutrition 0.000 description 1
229920000615 alginic acid Polymers 0.000 description 1
125000004183 alkoxy alkyl group Chemical group 0.000 description 1
150000001351 alkyl iodides Chemical class 0.000 description 1
239000002168 alkylating agent Substances 0.000 description 1
229940100198 alkylating agent Drugs 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
235000010210 aluminium Nutrition 0.000 description 1
235000012211 aluminium silicate Nutrition 0.000 description 1
239000003708 ampul Substances 0.000 description 1
125000003710 aryl alkyl group Chemical group 0.000 description 1
239000002585 base Substances 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
UQHXBABBJIBSCE-UHFFFAOYSA-N benzyl n-methyl-n-(4-methyl-1,3-oxazol-2-yl)carbamate Chemical compound N=1C(C)=COC=1N(C)C(=O)OCC1=CC=CC=C1 UQHXBABBJIBSCE-UHFFFAOYSA-N 0.000 description 1
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000000378 calcium silicate Substances 0.000 description 1
229910052918 calcium silicate Inorganic materials 0.000 description 1
235000012241 calcium silicate Nutrition 0.000 description 1
CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical class [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
235000013539 calcium stearate Nutrition 0.000 description 1
OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 description 1
239000002775 capsule Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000000969 carrier Substances 0.000 description 1
229940082500 cetostearyl alcohol Drugs 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
229940110456 cocoa butter Drugs 0.000 description 1
235000019868 cocoa butter Nutrition 0.000 description 1
238000001816 cooling Methods 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([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
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
239000008121 dextrose Substances 0.000 description 1
239000010432 diamond Substances 0.000 description 1
PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 1
229940042935 dichlorodifluoromethane Drugs 0.000 description 1
235000019404 dichlorodifluoromethane Nutrition 0.000 description 1
229940087091 dichlorotetrafluoroethane Drugs 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
229940116333 ethyl lactate Drugs 0.000 description 1
RZIZBJIRZVLHBL-UHFFFAOYSA-N ethyl n-butyl-n-[4-(hydroxymethyl)-1,3-oxazol-2-yl]carbamate Chemical compound CCCCN(C(=O)OCC)C1=NC(CO)=CO1 RZIZBJIRZVLHBL-UHFFFAOYSA-N 0.000 description 1
YDHXEEIUWSINAG-UHFFFAOYSA-N ethyl n-cyclohexyl-n-(4-methyl-1,3-oxazol-2-yl)carbamate Chemical compound N=1C(C)=COC=1N(C(=O)OCC)C1CCCCC1 YDHXEEIUWSINAG-UHFFFAOYSA-N 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
239000007902 hard capsule Substances 0.000 description 1
150000002391 heterocyclic compounds Chemical class 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
238000001802 infusion Methods 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
238000001361 intraarterial administration Methods 0.000 description 1
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000011344 liquid material Substances 0.000 description 1
229940057995 liquid paraffin Drugs 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
239000000463 material Substances 0.000 description 1
239000002609 medium Substances 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
239000008108 microcrystalline cellulose Substances 0.000 description 1
235000019813 microcrystalline cellulose Nutrition 0.000 description 1
229940016286 microcrystalline cellulose Drugs 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
235000019426 modified starch Nutrition 0.000 description 1
BCXXNJCHMPDNCU-UHFFFAOYSA-N n-butyl-4-methyl-1,3-oxazol-2-amine Chemical compound CCCCNC1=NC(C)=CO1 BCXXNJCHMPDNCU-UHFFFAOYSA-N 0.000 description 1
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 1
239000002674 ointment Substances 0.000 description 1
229940055577 oleyl alcohol Drugs 0.000 description 1
XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
239000012188 paraffin wax Substances 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000000312 peanut oil Substances 0.000 description 1
125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
239000008024 pharmaceutical diluent Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
QVLTXCYWHPZMCA-UHFFFAOYSA-N po4-po4 Chemical compound OP(O)(O)=O.OP(O)(O)=O QVLTXCYWHPZMCA-UHFFFAOYSA-N 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
239000003380 propellant Substances 0.000 description 1
230000000069 prophylactic effect Effects 0.000 description 1
229960003415 propylparaben Drugs 0.000 description 1
230000001698 pyrogenic effect Effects 0.000 description 1
230000008707 rearrangement Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
239000012056 semi-solid material Substances 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
235000017550 sodium carbonate Nutrition 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000007901 soft capsule Substances 0.000 description 1
239000011343 solid material Substances 0.000 description 1
229960005078 sorbitan sesquioleate Drugs 0.000 description 1
235000019337 sorbitan trioleate Nutrition 0.000 description 1
229960000391 sorbitan trioleate Drugs 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008107 starch Substances 0.000 description 1
239000012058 sterile packaged powder Substances 0.000 description 1
239000006190 sub-lingual tablet Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
OULAJFUGPPVRBK-UHFFFAOYSA-N tetratriacontyl alcohol Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCO OULAJFUGPPVRBK-UHFFFAOYSA-N 0.000 description 1
229960004559 theobromine Drugs 0.000 description 1
CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
229940029284 trichlorofluoromethane Drugs 0.000 description 1
ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- 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
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/34—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
- C07D263/48—Nitrogen atoms not forming part of a nitro radical
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/14—Antitussive agents
- 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
- A61P37/08—Antiallergic agents

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (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)
Pulmonology (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Immunology (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)

CH1242678A 1975-05-02 1978-12-05 CH615429A5 (pt)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB18320/75A GB1543154A (en)	1975-05-02	1975-05-02	Urea and carbamate derivatives

Publications (1)

Publication Number	Publication Date
CH615429A5 true CH615429A5 (pt)	1980-01-31

Family

ID=10110462

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
CH520076A CH614435A5 (pt)	1975-05-02	1976-04-26
CH1242678A CH615429A5 (pt)	1975-05-02	1978-12-05

Family Applications Before (1)

Application Number	Title	Priority Date	Filing Date
CH520076A CH614435A5 (pt)	1975-05-02	1976-04-26

Country Status (31)

Country	Link
US (1)	US4259343A (pt)
JP (2)	JPS6014034B2 (pt)
AR (1)	AR217238A1 (pt)
AT (1)	AT345818B (pt)
AU (1)	AU501722B2 (pt)
BE (1)	BE841315A (pt)
BG (1)	BG27369A3 (pt)
CA (1)	CA1072103A (pt)
CH (2)	CH614435A5 (pt)
CS (1)	CS193073B2 (pt)
DD (1)	DD126046A5 (pt)
DE (1)	DE2618547A1 (pt)
DK (1)	DK196076A (pt)
ES (2)	ES447538A1 (pt)
FR (1)	FR2309224A1 (pt)
GB (1)	GB1543154A (pt)
GR (1)	GR59808B (pt)
HU (1)	HU175111B (pt)
IE (1)	IE42991B1 (pt)
IL (1)	IL49393A (pt)
MX (1)	MX3652E (pt)
NL (1)	NL7604659A (pt)
NZ (1)	NZ180577A (pt)
PH (1)	PH13956A (pt)
PL (1)	PL100371B1 (pt)
PT (1)	PT65047B (pt)
RO (1)	RO68527B (pt)
SE (1)	SE7604899L (pt)
SU (2)	SU627753A3 (pt)
YU (1)	YU109376A (pt)
ZA (1)	ZA762119B (pt)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPH0421401Y2 (pt) *	1985-08-14	1992-05-15
JPS6334839U (pt) *	1986-08-26	1988-03-05

Family Cites Families (12)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CH66A (de) *		1889-01-08	J Kobler	Feueranzünder
CH58A (de) *		1889-01-08	F Bachschmid	Neuerung an Ankerhemmungen
CH70A (fr) *	1888-11-15	1889-01-09	Louis Carpano	Fraises à arrondir les roues d'horlogerie
CH75A (fr) *	1888-11-17	1889-01-09	A Bauer & Cie Soc	Machine à bourrer les cigarettes
US3290326A (en) *	1963-09-20	1966-12-06	Hoffmann La Roche	Esters of 4-lower alkyl-5-oxazole-car-bamic acid and intermediates therefor
IL28803A (en) *	1966-11-18	1974-05-16	Wyeth John & Brother Ltd	Oxazole and thiazole compounds,their preparation and pharmaceutical compositions containing them
US3682945A (en) *	1968-07-05	1972-08-08	Exxon Research Engineering Co	Certain 2-acylamino-4,5,6,7-tetrahydrobenzothiazoles
US3705903A (en) *	1969-07-22	1972-12-12	Lilly Industries Ltd	2-carbamido and thiocarbamido oxazoles
GB1310224A (en) *	1969-07-22	1973-03-14	Lilly Industries Ltd	Oxazole thioureas
GB1327042A (en) *	1969-11-05	1973-08-15	Lilly Industries Ltd	Oxazole derivatives their preparation and pharmaceutical compositions containing the same
US3697436A (en) *	1969-11-26	1972-10-10	Atomic Energy Commission	Production of uranium and plutonium carbides and nitrides
US3809755A (en) *	1970-11-09	1974-05-07	Lilly Industries Ltd	Certain 2-oxazolylthioureas as fungicides

1975
- 1975-05-02 GB GB18320/75A patent/GB1543154A/en not_active Expired
1976
- 1976-04-05 IE IE706/76A patent/IE42991B1/en unknown
- 1976-04-08 ZA ZA762119A patent/ZA762119B/xx unknown
- 1976-04-12 CA CA250,052A patent/CA1072103A/en not_active Expired
- 1976-04-12 IL IL49393A patent/IL49393A/xx unknown
- 1976-04-12 NZ NZ180577A patent/NZ180577A/xx unknown
- 1976-04-15 GR GR50550A patent/GR59808B/el unknown
- 1976-04-16 BG BG032931A patent/BG27369A3/xx unknown
- 1976-04-26 CH CH520076A patent/CH614435A5/xx not_active IP Right Cessation
- 1976-04-27 AR AR263051A patent/AR217238A1/es active
- 1976-04-27 PL PL1976189096A patent/PL100371B1/pl unknown
- 1976-04-28 DE DE19762618547 patent/DE2618547A1/de not_active Withdrawn
- 1976-04-28 SE SE7604899A patent/SE7604899L/xx unknown
- 1976-04-28 PT PT65047A patent/PT65047B/pt unknown
- 1976-04-29 FR FR7612696A patent/FR2309224A1/fr active Granted
- 1976-04-29 YU YU01093/76A patent/YU109376A/xx unknown
- 1976-04-29 NL NL7604659A patent/NL7604659A/xx not_active Application Discontinuation
- 1976-04-29 AT AT313676A patent/AT345818B/de not_active IP Right Cessation
- 1976-04-29 BE BE6045471A patent/BE841315A/xx not_active IP Right Cessation
- 1976-04-29 RO RO85940A patent/RO68527B/ro unknown
- 1976-04-29 MX MX76203U patent/MX3652E/es unknown
- 1976-04-29 CS CS762825A patent/CS193073B2/cs unknown
- 1976-04-30 ES ES447538A patent/ES447538A1/es not_active Expired
- 1976-04-30 DD DD192625A patent/DD126046A5/xx unknown
- 1976-04-30 DK DK196076A patent/DK196076A/da not_active Application Discontinuation
- 1976-04-30 HU HU76LI290A patent/HU175111B/hu unknown
- 1976-04-30 JP JP51050709A patent/JPS6014034B2/ja not_active Expired
- 1976-04-30 PH PH18389A patent/PH13956A/en unknown
- 1976-04-30 SU SU762353464A patent/SU627753A3/ru active
- 1976-05-03 AU AU13590/76A patent/AU501722B2/en not_active Expired
1977
- 1977-01-28 SU SU772445100A patent/SU645572A3/ru active
- 1977-07-14 ES ES460764A patent/ES460764A1/es not_active Expired
1978
- 1978-12-05 CH CH1242678A patent/CH615429A5/fr not_active IP Right Cessation
1979
- 1979-02-05 US US06/009,335 patent/US4259343A/en not_active Expired - Lifetime
1984
- 1984-04-11 JP JP59072576A patent/JPS59210072A/ja active Pending

Also Published As

Publication number	Publication date
GR59808B (en)	1978-03-01
CS193073B2 (en)	1979-09-17
PH13956A (en)	1980-11-12
US4259343A (en)	1981-03-31
SE7604899L (sv)	1976-11-03
AU1359076A (en)	1977-11-10
CA1072103A (en)	1980-02-19
IL49393A0 (en)	1976-06-30
NZ180577A (en)	1978-04-03
JPS59210072A (ja)	1984-11-28
YU109376A (en)	1982-08-31
PT65047B (en)	1978-08-02
ES460764A1 (es)	1978-05-01
FR2309224A1 (fr)	1976-11-26
DE2618547A1 (de)	1976-11-18
GB1543154A (en)	1979-03-28
NL7604659A (nl)	1976-11-04
IE42991L (en)	1976-11-02
IE42991B1 (en)	1980-12-03
AT345818B (de)	1978-10-10
ES447538A1 (es)	1977-11-16
RO68527B (ro)	1983-04-30
FR2309224B1 (pt)	1978-11-17
CH614435A5 (pt)	1979-11-30
JPS6014034B2 (ja)	1985-04-11
MX3652E (es)	1981-04-14
JPS51136667A (en)	1976-11-26
AU501722B2 (en)	1979-06-28
RO68527A (ro)	1983-04-29
SU645572A3 (ru)	1979-01-30
DD126046A5 (pt)	1977-06-15
PL100371B1 (pl)	1978-09-30
BG27369A3 (en)	1979-10-12
ATA313676A (de)	1978-02-15
IL49393A (en)	1979-09-30
DK196076A (da)	1976-11-03
SU627753A3 (ru)	1978-10-05
HU175111B (hu)	1980-05-28
PT65047A (en)	1976-05-01
ZA762119B (en)	1977-04-27
AR217238A1 (es)	1980-03-14
BE841315A (fr)	1976-10-29

Publication	Publication Date	Title
EP0074304B1 (fr)	1985-04-03	Ethers tricycliques, leur préparation et les compositions pharmaceutiques les contenant
EP0534859B1 (fr)	1994-11-17	3-Benzazépin-zones substituées par un groupe benzocyclobutyl- ou indanyl-alkyl-amino-alkyle, utiles dans le traitement des affections cardiovasculaires
FR2612516A1 (fr)	1988-09-23	Derives de benzoxazole et preparation les contenant
EP0834508A1 (fr)	1998-04-08	Nouveaux dérivés substitués de biphényle ou de phénylpyridine, leur procédé de préparation et les compositions pharmaceutiques qui les contiennent
CH643546A5 (fr)	1984-06-15	Procede pour la preparation de derives d'hydantoine.
KR100335169B1 (ko)	2002-05-04	포화 고리를 갖는 신규한 트리시클릭 화합물 및 이를포함하는 의약 조성물
FR2669927A1 (fr)	1992-06-05	Nouveaux derives de guanidine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent.
EP0109866B1 (fr)	1987-08-19	Nouveaux dérivés de la sulfonylurée, leurs procédés de préparation et les compositions pharmaceutiques les renfermant
US4139538A (en)	1979-02-13	Oxazolidinones as therapeutic agents
CH616933A5 (en)	1980-04-30	Heterocyclic compounds substituted by acylamino groups and process for their preparation
EP0348257A2 (fr)	1989-12-27	Nouveaux dérivés d'(hétéro)aryl diazole, leur procédé de préparation et leur application en thérapeutique
EP0719775A1 (fr)	1996-07-03	Dérivés de Phényl-4-thiazoles substitués, procédé pour leur préparation et compositions pharmaceutiques les contenant
CA2058878A1 (fr)	1992-07-09	Derives de benzisoxazole et de benzisothiazole, leur procede de preparation et les compositions pharmaceutiques les renfermant
FR2613717A1 (fr)	1988-10-14	Derives d'acides pyrimidinecarboxyliques, a action therapeutique
FR2660657A1 (fr)	1991-10-11	Nouveaux derives du 3-aminochromane, leur procede de preparation et les compositions pharmaceutiques qui les contiennent.
CH615429A5 (pt)	1980-01-31
EP0710658B1 (fr)	2001-10-04	Nouvelles 5-(aryloxymethyl)oxazolines, leur procédé de préparation et les compositions pharmaceutiques qui les contiennent
EP0463944A1 (fr)	1992-01-02	Acyl benzoxazolinones, leur procédé de préparation et les compositions pharmaceutiques qui les contiennent
EP0117961B1 (fr)	1991-04-03	Nouveaux dérivés hétérocycliques substitués par un radical aminé, leurs procédé d'obtention et les compositions pharmaceutiques en renfermant
EP0119896B1 (fr)	1986-10-08	Nouveaux dérivés de l'amino-5 dithiole-1,2 one-3, leur préparation et les compositions médicinales qui les contiennent
EP0105881B1 (fr)	1987-12-23	Nouvelles cyanoguanidines, leur procede d'obtention et les compositions pharmaceutiques en renfermant
BE1004489A3 (fr)	1992-12-01	Derives de dihydropyrimidothiazine, leur procede de preparation et compositions pharmaceutiques les contenant.
FR2719047A1 (fr)	1995-10-27	Nouveaux dérivés de benzylamines, leur procédé de fabrication et les compositions pharmaceutiques les renfermant.
US3865823A (en)	1975-02-11	(2-Nitro-1-imidazolyl)-carbamates
CA2596156A1 (fr)	2006-08-03	Nouveaux derives d'oximes heterocycliques, leur procede de preparation et les compositions pharmaceutiques qui les contiennent

Legal Events

Date	Code	Title	Description
1986-12-31	PL	Patent ceased
2024-10-31	PL	Patent ceased