DE2625285A1 - Heteroarylverbindungen, verfahren zu ihrer herstellung und sie enthaltende pharmazeutische mittel - Google Patents

Heteroarylverbindungen, verfahren zu ihrer herstellung und sie enthaltende pharmazeutische mittel

Info

Publication number: DE2625285A1
Authority: DE; Germany
Prior art keywords: alkyl; methyl; optionally substituted; cycloalkyl; ring
Prior art date: 1975-06-05
Legal status (The legal status 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 status listed.): Ceased

Application number

DE19762625285

Other languages

German (de)

English (en)

Inventor

William James Ross

John Pomfret Verge

William Robert Nige Williamson

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Lilly Industries Ltd

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.)

1975-06-05

Filing date

1976-06-04

Publication date

1976-12-23

1976-06-04 Application filed by Lilly Industries Ltd filed Critical Lilly Industries Ltd

1976-12-23 Publication of DE2625285A1 publication Critical patent/DE2625285A1/de

Status Ceased legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 title description 70
238000000034 method Methods 0.000 title description 21
239000000825 pharmaceutical preparation Substances 0.000 title description 2
238000004519 manufacturing process Methods 0.000 title 1
229940127557 pharmaceutical product Drugs 0.000 title 1
-1 η-butyl Chemical group 0.000 description 53
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 42
239000000243 solution Substances 0.000 description 37
238000004458 analytical method Methods 0.000 description 30
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
239000000203 mixture Substances 0.000 description 22
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
239000007787 solid Substances 0.000 description 17
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
239000004480 active ingredient Substances 0.000 description 14
125000000217 alkyl group Chemical group 0.000 description 13
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
239000003921 oil Substances 0.000 description 12
235000019198 oils Nutrition 0.000 description 12
125000001072 heteroaryl group Chemical group 0.000 description 11
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 11
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
238000009835 boiling Methods 0.000 description 10
239000007788 liquid Substances 0.000 description 10
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
239000003814 drug Substances 0.000 description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
239000008177 pharmaceutical agent Substances 0.000 description 8
238000002360 preparation method Methods 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
229940079593 drug Drugs 0.000 description 7
229910052736 halogen Inorganic materials 0.000 description 7
150000002367 halogens Chemical class 0.000 description 7
239000003208 petroleum Substances 0.000 description 7
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
239000011541 reaction mixture Substances 0.000 description 7
229920006395 saturated elastomer Polymers 0.000 description 7
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
239000004255 Butylated hydroxyanisole Substances 0.000 description 6
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
229940043253 butylated hydroxyanisole Drugs 0.000 description 6
235000019282 butylated hydroxyanisole Nutrition 0.000 description 6
CZBZUDVBLSSABA-UHFFFAOYSA-N butylated hydroxyanisole Chemical compound COC1=CC=C(O)C(C(C)(C)C)=C1.COC1=CC=C(O)C=C1C(C)(C)C CZBZUDVBLSSABA-UHFFFAOYSA-N 0.000 description 6
239000000460 chlorine Substances 0.000 description 6
238000001816 cooling Methods 0.000 description 6
125000005842 heteroatom Chemical group 0.000 description 6
239000003826 tablet Substances 0.000 description 6
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 5
206010020751 Hypersensitivity Diseases 0.000 description 5
208000026935 allergic disease Diseases 0.000 description 5
HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 5
239000002775 capsule Substances 0.000 description 5
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 5
239000000047 product Substances 0.000 description 5
238000003756 stirring Methods 0.000 description 5
239000000829 suppository Substances 0.000 description 5
HMPUHXCGUHDVBI-UHFFFAOYSA-N 5-methyl-1,3,4-thiadiazol-2-amine Chemical compound CC1=NN=C(N)S1 HMPUHXCGUHDVBI-UHFFFAOYSA-N 0.000 description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
230000010933 acylation Effects 0.000 description 4
238000005917 acylation reaction Methods 0.000 description 4
150000001412 amines Chemical class 0.000 description 4
125000004429 atom Chemical group 0.000 description 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
125000004432 carbon atom Chemical group C* 0.000 description 4
125000000753 cycloalkyl group Chemical group 0.000 description 4
PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 4
235000019404 dichlorodifluoromethane Nutrition 0.000 description 4
238000011049 filling Methods 0.000 description 4
239000007903 gelatin capsule Substances 0.000 description 4
230000009610 hypersensitivity Effects 0.000 description 4
239000012442 inert solvent Substances 0.000 description 4
239000004615 ingredient Substances 0.000 description 4
LSACYLWPPQLVSM-UHFFFAOYSA-N isobutyric acid anhydride Chemical compound CC(C)C(=O)OC(=O)C(C)C LSACYLWPPQLVSM-UHFFFAOYSA-N 0.000 description 4
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
150000003951 lactams Chemical group 0.000 description 4
229940057995 liquid paraffin Drugs 0.000 description 4
229910052943 magnesium sulfate Inorganic materials 0.000 description 4
235000019341 magnesium sulphate Nutrition 0.000 description 4
125000004433 nitrogen atom Chemical group N* 0.000 description 4
150000004866 oxadiazoles Chemical class 0.000 description 4
150000003839 salts Chemical class 0.000 description 4
239000000377 silicon dioxide Substances 0.000 description 4
125000001424 substituent group Chemical group 0.000 description 4
229910052717 sulfur Inorganic materials 0.000 description 4
239000000725 suspension Substances 0.000 description 4
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
IQXJCCZJOIKIAD-UHFFFAOYSA-N 1-(2-methoxyethoxy)hexadecane Chemical compound CCCCCCCCCCCCCCCCOCCOC IQXJCCZJOIKIAD-UHFFFAOYSA-N 0.000 description 3
VMZCDNSFRSVYKQ-UHFFFAOYSA-N 2-phenylacetyl chloride Chemical compound ClC(=O)CC1=CC=CC=C1 VMZCDNSFRSVYKQ-UHFFFAOYSA-N 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-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
229920000168 Microcrystalline cellulose Polymers 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
SKZKKFZAGNVIMN-UHFFFAOYSA-N Salicilamide Chemical compound NC(=O)C1=CC=CC=C1O SKZKKFZAGNVIMN-UHFFFAOYSA-N 0.000 description 3
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
229920002472 Starch Polymers 0.000 description 3
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
230000001154 acute effect Effects 0.000 description 3
125000004442 acylamino group Chemical group 0.000 description 3
239000000443 aerosol Substances 0.000 description 3
150000001408 amides Chemical class 0.000 description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
239000002585 base Substances 0.000 description 3
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
229950009789 cetomacrogol 1000 Drugs 0.000 description 3
229940082500 cetostearyl alcohol Drugs 0.000 description 3
229910052801 chlorine Inorganic materials 0.000 description 3
238000004440 column chromatography Methods 0.000 description 3
239000006071 cream Substances 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
229920000159 gelatin Polymers 0.000 description 3
235000019322 gelatine Nutrition 0.000 description 3
LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 description 3
239000008101 lactose Substances 0.000 description 3
235000019359 magnesium stearate Nutrition 0.000 description 3
239000008108 microcrystalline cellulose Substances 0.000 description 3
229940016286 microcrystalline cellulose Drugs 0.000 description 3
235000019813 microcrystalline cellulose Nutrition 0.000 description 3
GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 3
239000002674 ointment Substances 0.000 description 3
239000001301 oxygen Substances 0.000 description 3
229910052760 oxygen Inorganic materials 0.000 description 3
239000012188 paraffin wax Substances 0.000 description 3
229910000033 sodium borohydride Inorganic materials 0.000 description 3
239000012279 sodium borohydride Substances 0.000 description 3
235000019698 starch Nutrition 0.000 description 3
239000008107 starch Substances 0.000 description 3
239000011593 sulfur Substances 0.000 description 3
OULAJFUGPPVRBK-UHFFFAOYSA-N tetratriacontyl alcohol Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCO OULAJFUGPPVRBK-UHFFFAOYSA-N 0.000 description 3
230000001225 therapeutic effect Effects 0.000 description 3
125000004520 1,3,4-thiadiazolyl group Chemical group 0.000 description 2
ZHFWJCUKKDMFIV-UHFFFAOYSA-N 3-methyl-5-(trichloromethyl)-1,2,4-oxadiazole Chemical compound CC1=NOC(C(Cl)(Cl)Cl)=N1 ZHFWJCUKKDMFIV-UHFFFAOYSA-N 0.000 description 2
ILTLLMVRPBXCSX-UHFFFAOYSA-N 5-chloro-3-methyl-1,2,4-thiadiazole Chemical compound CC1=NSC(Cl)=N1 ILTLLMVRPBXCSX-UHFFFAOYSA-N 0.000 description 2
125000006163 5-membered heteroaryl group Chemical group 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
239000004338 Dichlorodifluoromethane Substances 0.000 description 2
239000001828 Gelatine Substances 0.000 description 2
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
ZTHYODDOHIVTJV-UHFFFAOYSA-N Propyl gallate Chemical compound CCCOC(=O)C1=CC(O)=C(O)C(O)=C1 ZTHYODDOHIVTJV-UHFFFAOYSA-N 0.000 description 2
239000002168 alkylating agent Substances 0.000 description 2
229940100198 alkylating agent Drugs 0.000 description 2
238000005804 alkylation reaction Methods 0.000 description 2
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
150000001721 carbon Chemical group 0.000 description 2
150000003857 carboxamides Chemical class 0.000 description 2
125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
238000002512 chemotherapy Methods 0.000 description 2
239000012230 colorless oil Substances 0.000 description 2
XRLDSWLMHUQECH-UHFFFAOYSA-N cyclopentanecarboxamide Chemical compound NC(=O)C1CCCC1 XRLDSWLMHUQECH-UHFFFAOYSA-N 0.000 description 2
ZOOSILUVXHVRJE-UHFFFAOYSA-N cyclopropanecarbonyl chloride Chemical compound ClC(=O)C1CC1 ZOOSILUVXHVRJE-UHFFFAOYSA-N 0.000 description 2
125000006255 cyclopropyl carbonyl group Chemical group [H]C1([H])C([H])([H])C1([H])C(*)=O 0.000 description 2
229940042935 dichlorodifluoromethane Drugs 0.000 description 2
229940087091 dichlorotetrafluoroethane Drugs 0.000 description 2
239000003085 diluting agent Substances 0.000 description 2
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
239000003937 drug carrier 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
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
125000005843 halogen group Chemical group 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
238000002329 infrared spectrum Methods 0.000 description 2
238000002347 injection Methods 0.000 description 2
239000007924 injection Substances 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
UORYIBWIZZBUSL-UHFFFAOYSA-N n-(5-methyl-1,3,4-thiadiazol-2-yl)hexanamide Chemical compound CCCCCC(=O)NC1=NN=C(C)S1 UORYIBWIZZBUSL-UHFFFAOYSA-N 0.000 description 2
NZKFOTZQIJUAHK-UHFFFAOYSA-N n-benzyl-5-methyl-1,3,4-thiadiazol-2-amine Chemical compound S1C(C)=NN=C1NCC1=CC=CC=C1 NZKFOTZQIJUAHK-UHFFFAOYSA-N 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 2
239000000546 pharmaceutical excipient Substances 0.000 description 2
RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 2
239000003380 propellant Substances 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
238000010992 reflux Methods 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
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
235000012239 silicon dioxide Nutrition 0.000 description 2
239000002904 solvent Substances 0.000 description 2
229910001220 stainless steel Inorganic materials 0.000 description 2
239000010935 stainless steel Substances 0.000 description 2
238000003786 synthesis reaction Methods 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
125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
238000002211 ultraviolet spectrum Methods 0.000 description 2
MEFKFJOEVLUFAY-UHFFFAOYSA-N (2,2,2-trichloroacetyl) 2,2,2-trichloroacetate Chemical compound ClC(Cl)(Cl)C(=O)OC(=O)C(Cl)(Cl)Cl MEFKFJOEVLUFAY-UHFFFAOYSA-N 0.000 description 1
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
125000004765 (C1-C4) haloalkyl group Chemical group 0.000 description 1
XEMRAKSQROQPBR-UHFFFAOYSA-N (trichloromethyl)benzene Chemical compound ClC(Cl)(Cl)C1=CC=CC=C1 XEMRAKSQROQPBR-UHFFFAOYSA-N 0.000 description 1
UGUHFDPGDQDVGX-UHFFFAOYSA-N 1,2,3-thiadiazole Chemical group C1=CSN=N1 UGUHFDPGDQDVGX-UHFFFAOYSA-N 0.000 description 1
125000004505 1,2,4-oxadiazol-5-yl group Chemical group O1N=CN=C1* 0.000 description 1
BBVIDBNAYOIXOE-UHFFFAOYSA-N 1,2,4-oxadiazole Chemical compound C=1N=CON=1 BBVIDBNAYOIXOE-UHFFFAOYSA-N 0.000 description 1
150000005071 1,2,4-oxadiazoles Chemical class 0.000 description 1
125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 description 1
YGTAZGSLCXNBQL-UHFFFAOYSA-N 1,2,4-thiadiazole Chemical class C=1N=CSN=1 YGTAZGSLCXNBQL-UHFFFAOYSA-N 0.000 description 1
125000004514 1,2,4-thiadiazolyl group Chemical group 0.000 description 1
ZPQYNOMPSLSWQH-UHFFFAOYSA-N 1-acetamido-3-propylurea Chemical compound CCCNC(=O)NNC(C)=O ZPQYNOMPSLSWQH-UHFFFAOYSA-N 0.000 description 1
CZLPCLANGIXFIE-UHFFFAOYSA-N 1-amino-3-prop-2-enylthiourea Chemical compound NNC(=S)NCC=C CZLPCLANGIXFIE-UHFFFAOYSA-N 0.000 description 1
125000001478 1-chloroethyl group Chemical group [H]C([H])([H])C([H])(Cl)* 0.000 description 1
NFDXQGNDWIPXQL-UHFFFAOYSA-N 1-cyclooctyldiazocane Chemical compound C1CCCCCCC1N1NCCCCCC1 NFDXQGNDWIPXQL-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
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
ZZCQZTDCUHBDGI-UHFFFAOYSA-N 3-methyl-n-[(4-methylphenyl)methyl]-1,2,4-oxadiazol-5-amine Chemical compound CC1=NOC(NCC=2C=CC(C)=CC=2)=N1 ZZCQZTDCUHBDGI-UHFFFAOYSA-N 0.000 description 1
MPVFHXLMJMBREB-UHFFFAOYSA-N 4-(5-methyl-1,3,4-thiadiazol-2-yl)butan-1-amine Chemical compound CC1=NN=C(CCCCN)S1 MPVFHXLMJMBREB-UHFFFAOYSA-N 0.000 description 1
125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 1
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
LJRUOAZKZFJJIJ-UHFFFAOYSA-N 5-methyl-n-propan-2-yl-1,3,4-thiadiazol-2-amine Chemical compound CC(C)NC1=NN=C(C)S1 LJRUOAZKZFJJIJ-UHFFFAOYSA-N 0.000 description 1
DDUHZTYCFQRHIY-UHFFFAOYSA-N 7-chloro-3',4,6-trimethoxy-5'-methylspiro[1-benzofuran-2,4'-cyclohex-2-ene]-1',3-dione Chemical compound COC1=CC(=O)CC(C)C11C(=O)C(C(OC)=CC(OC)=C2Cl)=C2O1 DDUHZTYCFQRHIY-UHFFFAOYSA-N 0.000 description 1
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 1
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ZZXHZGBFNAUJGI-UHFFFAOYSA-N n-methyl-n-(3-methyl-1,2,4-thiadiazol-5-yl)cyclohexanecarboxamide Chemical compound N=1C(C)=NSC=1N(C)C(=O)C1CCCCC1 ZZXHZGBFNAUJGI-UHFFFAOYSA-N 0.000 description 1
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239000012074 organic phase Substances 0.000 description 1
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QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
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239000008194 pharmaceutical composition Substances 0.000 description 1
239000008024 pharmaceutical diluent Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
229920006316 polyvinylpyrrolidine Polymers 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
230000000069 prophylactic effect Effects 0.000 description 1
239000000473 propyl gallate Substances 0.000 description 1
235000010388 propyl gallate Nutrition 0.000 description 1
229940075579 propyl gallate Drugs 0.000 description 1
QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 1
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239000012056 semi-solid material Substances 0.000 description 1
239000011734 sodium Substances 0.000 description 1
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239000012312 sodium hydride Substances 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000011343 solid material Substances 0.000 description 1
229960005078 sorbitan sesquioleate Drugs 0.000 description 1
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239000012058 sterile packaged powder Substances 0.000 description 1
239000006190 sub-lingual tablet Substances 0.000 description 1
239000000758 substrate Substances 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
238000010189 synthetic method Methods 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
VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
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235000010487 tragacanth Nutrition 0.000 description 1
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QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 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
238000005406 washing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
- C07D271/07—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/10—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles
- C07D271/113—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/08—1,2,4-Thiadiazoles; Hydrogenated 1,2,4-thiadiazoles
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
- C07D285/125—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
- C07D285/135—Nitrogen atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Plural Heterocyclic Compounds (AREA)

DE19762625285 1975-06-05 1976-06-04 Heteroarylverbindungen, verfahren zu ihrer herstellung und sie enthaltende pharmazeutische mittel Ceased DE2625285A1 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB24224/75A GB1551735A (en)	1975-06-05	1975-06-05	Acylated aminothiazoles and aminooxadiazoles

Publications (1)

Publication Number	Publication Date
DE2625285A1 true DE2625285A1 (de)	1976-12-23

Family

ID=10208350

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DE19762625285 Ceased DE2625285A1 (de)	1975-06-05	1976-06-04	Heteroarylverbindungen, verfahren zu ihrer herstellung und sie enthaltende pharmazeutische mittel

Country Status (34)

Country	Link
JP (1)	JPS51146468A (no)
AR (1)	AR217240A1 (no)
AT (1)	AT346843B (no)
AU (1)	AU503150B2 (no)
BE (1)	BE842579A (no)
BG (1)	BG27359A3 (no)
CA (1)	CA1085860A (no)
CH (2)	CH612427A5 (no)
CS (1)	CS200494B2 (no)
DD (1)	DD125075A5 (no)
DE (1)	DE2625285A1 (no)
DK (1)	DK243276A (no)
EG (1)	EG12226A (no)
ES (1)	ES448590A1 (no)
FI (1)	FI63394C (no)
FR (1)	FR2313049A1 (no)
GB (1)	GB1551735A (no)
GR (1)	GR60380B (no)
HU (1)	HU174191B (no)
IE (1)	IE43474B1 (no)
IL (1)	IL49692A (no)
LU (1)	LU75070A1 (no)
MX (1)	MX3483E (no)
NL (1)	NL7606178A (no)
NO (1)	NO144346C (no)
NZ (1)	NZ181011A (no)
OA (1)	OA05346A (no)
PH (1)	PH16077A (no)
PL (1)	PL103004B1 (no)
PT (1)	PT65182B (no)
SE (1)	SE428561B (no)
SU (1)	SU639451A3 (no)
YU (1)	YU137176A (no)
ZA (1)	ZA763209B (no)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0003539A2 (de) *	1978-02-10	1979-08-22	Bayer Ag	N-Azolylalkyl-halogenacetanilide, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Herbizide
EP0003540A2 (de)	1978-02-10	1979-08-22	Bayer Ag	N-Azolylalkyl-aniline sowie Verfahren zu ihrer Herstellung
EP0023539A1 (de) *	1979-05-18	1981-02-11	Ciba-Geigy Ag	3-(N-1,3,4-Thiadiazolyl-2)-amino-alkyl-acrylsäurealkylester, Verfahren zu ihrer Herstellung und ihre Verwendung als Pflanzenbakterizide
US4427688A (en)	1981-05-25	1984-01-24	Basf Aktiengesellschaft	N-Substituted 2-methylnaphthylamides, their preparation, and their use for controlling fungi
WO2004065351A1 (en) *	2003-01-24	2004-08-05	Novartis Ag	Amide derivatives and their use as inhibitors of 11-beta-hydroxysteroid dehydrogenase type 1

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CH636866A5 (de) *	1977-08-15	1983-06-30	Lilly Co Eli	Thiadiazolylbenzamide und sie enthaltende insektizide mittel.
US4264616A (en) *	1980-08-29	1981-04-28	Gulf Oil Corporation	2-Iodoacetylimino-3-methyl-5-trifluoromethyl-1,3,4-thiadiazol-4-ine and use as a fungicide
MA19269A1 (fr) *	1980-09-16	1982-04-01	Lilly Co Eli	Perfectionnement relatif a des derives de n-arylbenzamides .
US4874864A (en) *	1988-05-24	1989-10-17	Pfizer Inc.	Benzamide protease inhibitors
WO2001046165A2 (en) *	1999-12-16	2001-06-28	Novartis Ag	N-heteroaryl-amides and their use as parasiticides
RU2448961C1 (ru) *	2011-02-03	2012-04-27	Открытое акционерное общество "Всероссийский научный центр по безопасности биологически активных веществ" (ОАО "ВНЦ БАВ")	Фармацевтическая композиция, обладающая противовоспалительной, бронхолитической, противотуберкулезной активностями

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3720684A (en) *	1970-10-13	1973-03-13	Velsicol Chemical Corp	5-halo-1,2,4-thiadiazoles
IL35743A (en) *	1970-11-27	1974-10-22	Peretz B	3-isopropyl-5-amino-1,2,4-thiadiazole compounds

1975
- 1975-06-05 GB GB24224/75A patent/GB1551735A/en not_active Expired
1976
- 1976-05-31 FR FR7616338A patent/FR2313049A1/fr active Granted
- 1976-05-31 CA CA253,755A patent/CA1085860A/en not_active Expired
- 1976-05-31 IE IE1148/76A patent/IE43474B1/en unknown
- 1976-05-31 IL IL49692A patent/IL49692A/xx unknown
- 1976-05-31 NZ NZ181011A patent/NZ181011A/xx unknown
- 1976-06-01 AR AR263474A patent/AR217240A1/es active
- 1976-06-01 ZA ZA00763209A patent/ZA763209B/xx unknown
- 1976-06-01 GR GR50868A patent/GR60380B/el unknown
- 1976-06-01 CH CH685576A patent/CH612427A5/xx not_active IP Right Cessation
- 1976-06-02 SE SE7606226A patent/SE428561B/xx unknown
- 1976-06-02 LU LU75070A patent/LU75070A1/xx unknown
- 1976-06-02 DK DK243276A patent/DK243276A/da not_active Application Discontinuation
- 1976-06-03 AU AU14619/76A patent/AU503150B2/en not_active Expired
- 1976-06-03 YU YU01371/76A patent/YU137176A/xx unknown
- 1976-06-03 HU HU76LI293A patent/HU174191B/hu unknown
- 1976-06-03 BE BE6045539A patent/BE842579A/xx not_active IP Right Cessation
- 1976-06-03 CS CS763692A patent/CS200494B2/cs unknown
- 1976-06-03 PT PT65182A patent/PT65182B/pt unknown
- 1976-06-04 NO NO761913A patent/NO144346C/no unknown
- 1976-06-04 PH PH18535A patent/PH16077A/en unknown
- 1976-06-04 FI FI761585A patent/FI63394C/fi not_active IP Right Cessation
- 1976-06-04 BG BG033366A patent/BG27359A3/xx unknown
- 1976-06-04 ES ES448590A patent/ES448590A1/es not_active Expired
- 1976-06-04 DE DE19762625285 patent/DE2625285A1/de not_active Ceased
- 1976-06-04 MX MX000265U patent/MX3483E/es unknown
- 1976-06-04 PL PL1976190132A patent/PL103004B1/pl unknown
- 1976-06-04 DD DD193198A patent/DD125075A5/xx unknown
- 1976-06-04 JP JP51066027A patent/JPS51146468A/ja active Pending
- 1976-06-04 SU SU762366751A patent/SU639451A3/ru active
- 1976-06-04 AT AT412276A patent/AT346843B/de not_active IP Right Cessation
- 1976-06-05 OA OA55843A patent/OA05346A/xx unknown
- 1976-06-05 EG EG76334A patent/EG12226A/xx active
- 1976-06-08 NL NL7606178A patent/NL7606178A/xx not_active Application Discontinuation
1979
- 1979-01-10 CH CH20579A patent/CH616933A5/fr not_active IP Right Cessation

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0003539A2 (de) *	1978-02-10	1979-08-22	Bayer Ag	N-Azolylalkyl-halogenacetanilide, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Herbizide
EP0003540A2 (de)	1978-02-10	1979-08-22	Bayer Ag	N-Azolylalkyl-aniline sowie Verfahren zu ihrer Herstellung
EP0003539A3 (en) *	1978-02-10	1979-09-05	Bayer Aktiengesellschaft	N-azolylalkyl-halogenoacetanilides, process for their preparation and their use as herbicides
US4267338A (en) *	1978-02-10	1981-05-12	Bayer Aktiengesellschaft	N-Azolylalkyl-anilines
EP0023539A1 (de) *	1979-05-18	1981-02-11	Ciba-Geigy Ag	3-(N-1,3,4-Thiadiazolyl-2)-amino-alkyl-acrylsäurealkylester, Verfahren zu ihrer Herstellung und ihre Verwendung als Pflanzenbakterizide
US4427688A (en)	1981-05-25	1984-01-24	Basf Aktiengesellschaft	N-Substituted 2-methylnaphthylamides, their preparation, and their use for controlling fungi
WO2004065351A1 (en) *	2003-01-24	2004-08-05	Novartis Ag	Amide derivatives and their use as inhibitors of 11-beta-hydroxysteroid dehydrogenase type 1

Also Published As

Publication number	Publication date
PL103004B1 (pl)	1979-05-31
LU75070A1 (no)	1978-01-18
NO144346C (no)	1981-08-12
FI761585A (no)	1976-12-06
CA1085860A (en)	1980-09-16
CH612427A5 (en)	1979-07-31
PT65182A (en)	1976-07-01
YU137176A (en)	1982-10-31
CS200494B2 (en)	1980-09-15
BE842579A (fr)	1976-12-03
AU503150B2 (en)	1979-08-23
PT65182B (en)	1978-11-06
ES448590A1 (es)	1977-11-16
JPS51146468A (en)	1976-12-16
MX3483E (es)	1980-12-16
HU174191B (hu)	1979-11-28
PH16077A (en)	1983-06-20
IL49692A0 (en)	1976-08-31
NL7606178A (nl)	1976-12-07
FI63394B (fi)	1983-02-28
IE43474L (en)	1976-12-05
NZ181011A (en)	1978-11-13
SE7606226L (sv)	1976-12-06
FR2313049A1 (fr)	1976-12-31
ATA412276A (de)	1978-04-15
SU639451A3 (ru)	1978-12-25
AT346843B (de)	1978-11-27
AU1461976A (en)	1977-12-08
NO761913L (no)	1976-12-07
FI63394C (fi)	1983-06-10
SE428561B (sv)	1983-07-11
CH616933A5 (en)	1980-04-30
OA05346A (fr)	1981-02-28
DK243276A (da)	1976-12-06
BG27359A3 (en)	1979-10-12
IE43474B1 (en)	1981-03-11
GR60380B (en)	1978-05-23
ZA763209B (en)	1978-01-25
DD125075A5 (no)	1977-03-30
FR2313049B1 (no)	1978-12-15
GB1551735A (en)	1979-09-12
NO144346B (no)	1981-05-04
IL49692A (en)	1980-07-31
EG12226A (en)	1978-12-31
AR217240A1 (es)	1980-03-14

Publication	Publication Date	Title
DE68914029T2 (de)	1994-07-07	Arylmethylenderivate von Thiazolidinonen, Imidazolidinonen und Oxazolidininonen, nützlich als antiallergische Wirkstoffe und antiinflammatorische Wirkstoffe.
US3055907A (en)	1962-09-25	Acyl benzimidazoles and method of preparing same
DE2951675C2 (de)	1982-07-01	Guanidinothiazolverbindungen, Verfahren zu deren Herstellung und Arzneimittelzubereitungen
US3029189A (en)	1962-04-10	S-aryl-z-mno-x-qxazolibinones
US3852293A (en)	1974-12-03	4-phenyl-2-(3-pyridyl)-thiazole carboxamides
PT99351A (pt)	1992-09-30	Processo para a preparacao de derivados de tiazolidinodiona
DE2625285A1 (de)	1976-12-23	Heteroarylverbindungen, verfahren zu ihrer herstellung und sie enthaltende pharmazeutische mittel
US3419575A (en)	1968-12-31	Novel 2-amino-5-aminoalkyl-thiadiazoles
US3755587A (en)	1973-08-28	Compositions and methods for lowering blood sugar using aryl sulphonylsemicarbazides containing heterocyclic acylamino groups
DE2625242A1 (de)	1976-12-23	Heteroarylverbindungen, verfahren zu ihrer herstellung und sie enthaltende pharmazeutische mittel
DE2459380A1 (de)	1975-06-19	Verfahren zur herstellung von oxazolderivaten
US4450159A (en)	1984-05-22	Carbamic acid derivatives as selective immunosuppresive agents
US3290326A (en)	1966-12-06	Esters of 4-lower alkyl-5-oxazole-car-bamic acid and intermediates therefor
US3557099A (en)	1971-01-19	Nitrofuryl-oxadiazole derivatives
US4158659A (en)	1979-06-19	Acylamino derivatives
US3896223A (en)	1975-07-22	Anti-inflammatory thiazole compositions and methods for using same
US3879531A (en)	1975-04-22	2-aminothiazoles compositions and methods for using them as psychotherapeutic agents
US3933833A (en)	1976-01-20	Phenyl -thiourea, -carbothioamide and -carbonothioamide derivatives
US4246272A (en)	1981-01-20	Benzamidine derivatives
US4352929A (en)	1982-10-05	1,3-Thiazin-4-one
US5280043A (en)	1994-01-18	Sulphonamido containing phenylalkanoic acids as thromboxane A2 antagonists
EP0044266A2 (de)	1982-01-20	Neue substituierte 3,5-Diamino-1,2,4-oxadiazole und 3,5-Diamino-1,2,4-thiadiazole, Verfahren zu ihrer Herstellung und sie enthaltende pharmazeutische Präparate
US5240918A (en)	1993-08-31	2-(substituted imino)-thiazolidines and process for the preparation thereof
US4163048A (en)	1979-07-31	Acylamino-1,2,4-oxadiazole or thiadiazole derivatives as anti-hypersensitivity agents
GB1569238A (en)	1980-06-11	2,5-dihdro-1,2-thiazino(5,6-b)indol-3-carboxamide-1,1-dioxide derivatives

Legal Events

Date	Code	Title	Description
1983-07-21	8110	Request for examination paragraph 44
1984-12-06	8131	Rejection