NO128612B - - Google Patents
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- Publication number
- NO128612B NO128612B NO00165389A NO16538966A NO128612B NO 128612 B NO128612 B NO 128612B NO 00165389 A NO00165389 A NO 00165389A NO 16538966 A NO16538966 A NO 16538966A NO 128612 B NO128612 B NO 128612B
- Authority
- NO
- Norway
- Prior art keywords
- thiazolidinedione
- methyl
- general formula
- azine
- hydrogen
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 26
- 239000002253 acid Substances 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 17
- 150000002148 esters Chemical class 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 12
- 238000002360 preparation method Methods 0.000 claims description 10
- 150000002431 hydrogen Chemical class 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- -1 halogen hydrogen Chemical class 0.000 claims description 6
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 150000003931 anilides Chemical class 0.000 claims description 4
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 4
- 125000005907 alkyl ester group Chemical group 0.000 claims description 3
- 239000011230 binding agent Substances 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 150000003459 sulfonic acid esters Chemical class 0.000 claims description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 2
- 150000002429 hydrazines Chemical class 0.000 claims description 2
- KIWUVOGUEXMXSV-UHFFFAOYSA-N rhodanine Chemical compound O=C1CSC(=S)N1 KIWUVOGUEXMXSV-UHFFFAOYSA-N 0.000 claims description 2
- SRVJKTDHMYAMHA-WUXMJOGZSA-N thioacetazone Chemical compound CC(=O)NC1=CC=C(\C=N\NC(N)=S)C=C1 SRVJKTDHMYAMHA-WUXMJOGZSA-N 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
- ZOBPZXTWZATXDG-UHFFFAOYSA-N 1,3-thiazolidine-2,4-dione Chemical compound O=C1CSC(=O)N1 ZOBPZXTWZATXDG-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- LCUIYFVDGMBHBA-UHFFFAOYSA-N 3-prop-2-enyl-1,3-thiazolidine-2,4-dione Chemical compound C=CCN1C(=O)CSC1=O LCUIYFVDGMBHBA-UHFFFAOYSA-N 0.000 description 11
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- DWJMXHLXYSEPGR-UHFFFAOYSA-N 3,5-dimethyl-1,3-thiazolidine-2,4-dione Chemical compound CC1SC(=O)N(C)C1=O DWJMXHLXYSEPGR-UHFFFAOYSA-N 0.000 description 8
- HMLWNNMYODLLJO-UHFFFAOYSA-N 3-methyl-1,3-thiazolidine-2,4-dione Chemical compound CN1C(=O)CSC1=O HMLWNNMYODLLJO-UHFFFAOYSA-N 0.000 description 8
- PTXFGUVCXVEZET-UHFFFAOYSA-N 5-methyl-1,3-thiazolidine-2,4-dione Chemical compound CC1SC(=O)NC1=O PTXFGUVCXVEZET-UHFFFAOYSA-N 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 5
- 206010028980 Neoplasm Diseases 0.000 description 5
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 229940040526 anhydrous sodium acetate Drugs 0.000 description 4
- 239000000155 melt Substances 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 229910000104 sodium hydride Inorganic materials 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- KGRUGYASLHWXSH-UHFFFAOYSA-N 3-but-2-enyl-1,3-thiazolidine-2,4-dione Chemical compound C(C=CC)N1C(SCC1=O)=O KGRUGYASLHWXSH-UHFFFAOYSA-N 0.000 description 3
- LSHRASHLPXLEJD-UHFFFAOYSA-N 3-ethyl-5-methyl-1,3-thiazolidine-2,4-dione Chemical compound CCN1C(=O)SC(C)C1=O LSHRASHLPXLEJD-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- NZOJBLCFGXIWCG-UHFFFAOYSA-N C(C=CC)N1C(SC(C1=O)C)=O Chemical compound C(C=CC)N1C(SC(C1=O)C)=O NZOJBLCFGXIWCG-UHFFFAOYSA-N 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- OQNGCCWBHLEQFN-UHFFFAOYSA-N chloroform;hexane Chemical compound ClC(Cl)Cl.CCCCCC OQNGCCWBHLEQFN-UHFFFAOYSA-N 0.000 description 3
- BRWIZMBXBAOCCF-UHFFFAOYSA-N hydrazinecarbothioamide Chemical class NNC(N)=S BRWIZMBXBAOCCF-UHFFFAOYSA-N 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- KCOYHFNCTWXETP-UHFFFAOYSA-N (carbamothioylamino)thiourea Chemical compound NC(=S)NNC(N)=S KCOYHFNCTWXETP-UHFFFAOYSA-N 0.000 description 2
- GYGUTBCTEJBRAN-UHFFFAOYSA-N 3-prop-2-enyl-2-sulfanylidene-1,3-thiazolidin-4-one Chemical compound C=CCN1C(=O)CSC1=S GYGUTBCTEJBRAN-UHFFFAOYSA-N 0.000 description 2
- UXSCGMIIRKNSPZ-UHFFFAOYSA-N 5-methyl-3-pent-3-en-2-yl-1,3-thiazolidine-2,4-dione Chemical compound CC1C(N(C(S1)=O)C(C=CC)C)=O UXSCGMIIRKNSPZ-UHFFFAOYSA-N 0.000 description 2
- GVGRWLGUZTZMJR-UHFFFAOYSA-N 5-methyl-3-prop-2-ynyl-1,3-thiazolidine-2,4-dione Chemical compound C(C#C)N1C(SC(C1=O)C)=O GVGRWLGUZTZMJR-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 230000000840 anti-viral effect Effects 0.000 description 2
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 2
- 229940106681 chloroacetic acid Drugs 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 125000001475 halogen functional group Chemical group 0.000 description 2
- KDCIHNCMPUBDKT-UHFFFAOYSA-N hexane;propan-2-one Chemical compound CC(C)=O.CCCCCC KDCIHNCMPUBDKT-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000007920 subcutaneous administration Methods 0.000 description 2
- 230000007306 turnover Effects 0.000 description 2
- 230000003612 virological effect Effects 0.000 description 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- AVMHMVJVHYGDOO-NSCUHMNNSA-N (e)-1-bromobut-2-ene Chemical compound C\C=C\CBr AVMHMVJVHYGDOO-NSCUHMNNSA-N 0.000 description 1
- WFJFGMLKAISFOZ-UHFFFAOYSA-N 1-amino-3-iminourea Chemical compound NN=C(O)N=N WFJFGMLKAISFOZ-UHFFFAOYSA-N 0.000 description 1
- 150000001473 2,4-thiazolidinediones Chemical class 0.000 description 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- YAQLSKVCTLCIIE-UHFFFAOYSA-N 2-bromobutyric acid Chemical compound CCC(Br)C(O)=O YAQLSKVCTLCIIE-UHFFFAOYSA-N 0.000 description 1
- VONWPEXRCLHKRJ-UHFFFAOYSA-N 2-chloro-n-phenylacetamide Chemical compound ClCC(=O)NC1=CC=CC=C1 VONWPEXRCLHKRJ-UHFFFAOYSA-N 0.000 description 1
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 1
- FAZZDAHNCHFASH-UHFFFAOYSA-N 3-cyclohex-2-en-1-yl-5-methyl-1,3-thiazolidine-2,4-dione Chemical compound C1(C=CCCC1)N1C(SC(C1=O)C)=O FAZZDAHNCHFASH-UHFFFAOYSA-N 0.000 description 1
- IKQROFBYABVNTB-UHFFFAOYSA-N 3-ethyl-1,3-thiazolidine-2,4-dione Chemical compound CCN1C(=O)CSC1=O IKQROFBYABVNTB-UHFFFAOYSA-N 0.000 description 1
- AGUSZZRAQMEXDZ-UHFFFAOYSA-N 3-prop-2-ynyl-1,3-thiazolidine-2,4-dione Chemical compound O=C1CSC(=O)N1CC#C AGUSZZRAQMEXDZ-UHFFFAOYSA-N 0.000 description 1
- QGTAFNSUDGNGRJ-UHFFFAOYSA-N 5-ethyl-1,3-thiazolidine-2,4-dione Chemical compound CCC1SC(=O)NC1=O QGTAFNSUDGNGRJ-UHFFFAOYSA-N 0.000 description 1
- QFUWYUXQPJALGN-UHFFFAOYSA-N C(C)C1C(N(C(S1)=O)CC=CC)=O Chemical compound C(C)C1C(N(C(S1)=O)CC=CC)=O QFUWYUXQPJALGN-UHFFFAOYSA-N 0.000 description 1
- 201000009030 Carcinoma Diseases 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 229940123464 Thiazolidinedione Drugs 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 241000700605 Viruses Species 0.000 description 1
- 208000009916 Yoshida Sarcoma Diseases 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000001339 alkali metal compounds Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- HFEHLDPGIKPNKL-UHFFFAOYSA-N allyl iodide Chemical compound ICC=C HFEHLDPGIKPNKL-UHFFFAOYSA-N 0.000 description 1
- 229940051881 anilide analgesics and antipyretics Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 1
- 229940008406 diethyl sulfate Drugs 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 229940042396 direct acting antivirals thiosemicarbazones Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 206010014599 encephalitis Diseases 0.000 description 1
- 201000002491 encephalomyelitis Diseases 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 150000004694 iodide salts Chemical class 0.000 description 1
- SIAPCJWMELPYOE-UHFFFAOYSA-N lithium hydride Chemical compound [LiH] SIAPCJWMELPYOE-UHFFFAOYSA-N 0.000 description 1
- 229910000103 lithium hydride Inorganic materials 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 125000005948 methanesulfonyloxy group Chemical group 0.000 description 1
- 230000009826 neoplastic cell growth Effects 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical class OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- 150000003584 thiosemicarbazones Chemical class 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole 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
- C07D277/54—Nitrogen and either oxygen or sulfur atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Management, Administration, Business Operations System, And Electronic Commerce (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1498565A CH459216A (de) | 1965-10-29 | 1965-10-29 | Verfahren zur Herstellung von neuen Azinen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO128612B true NO128612B (en, 2012) | 1973-12-17 |
Family
ID=4405394
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO00165389A NO128612B (en, 2012) | 1965-10-29 | 1966-10-28 |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US3746717A (en, 2012) |
| AT (2) | AT263769B (en, 2012) |
| BE (1) | BE689020A (en, 2012) |
| BR (1) | BR6684131D0 (en, 2012) |
| CH (1) | CH459216A (en, 2012) |
| DE (1) | DE1695095C3 (en, 2012) |
| DK (1) | DK121170B (en, 2012) |
| ES (4) | ES332858A1 (en, 2012) |
| FI (1) | FI48739C (en, 2012) |
| FR (1) | FR6874M (en, 2012) |
| GB (1) | GB1122604A (en, 2012) |
| IL (1) | IL26768A (en, 2012) |
| NL (1) | NL149798B (en, 2012) |
| NO (1) | NO128612B (en, 2012) |
| SE (1) | SE346540B (en, 2012) |
| YU (3) | YU36726B (en, 2012) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0753147A1 (en) | 1994-03-30 | 1997-01-15 | Novartis AG | Screening method using the rzr receptor family |
-
1965
- 1965-10-29 CH CH1498565A patent/CH459216A/de unknown
-
1966
- 1966-10-27 FI FI662838A patent/FI48739C/fi active
- 1966-10-27 BR BR184131/66A patent/BR6684131D0/pt unknown
- 1966-10-28 ES ES0332858A patent/ES332858A1/es not_active Expired
- 1966-10-28 ES ES0332861A patent/ES332861A1/es not_active Expired
- 1966-10-28 GB GB48444/66A patent/GB1122604A/en not_active Expired
- 1966-10-28 BE BE689020D patent/BE689020A/xx unknown
- 1966-10-28 AT AT1005266A patent/AT263769B/de active
- 1966-10-28 IL IL26768A patent/IL26768A/xx unknown
- 1966-10-28 SE SE14844/66A patent/SE346540B/xx unknown
- 1966-10-28 DK DK562066AA patent/DK121170B/da unknown
- 1966-10-28 ES ES0332859A patent/ES332859A1/es not_active Expired
- 1966-10-28 AT AT675967A patent/AT267523B/de active
- 1966-10-28 NO NO00165389A patent/NO128612B/no unknown
- 1966-10-28 NL NL666615305A patent/NL149798B/xx not_active IP Right Cessation
- 1966-10-28 YU YU2035/66A patent/YU36726B/xx unknown
- 1966-10-28 ES ES0332860A patent/ES332860A1/es not_active Expired
- 1966-10-28 DE DE1695095A patent/DE1695095C3/de not_active Expired
-
1967
- 1967-01-26 FR FR92556A patent/FR6874M/fr not_active Expired
-
1971
- 1971-10-05 US US00186808A patent/US3746717A/en not_active Expired - Lifetime
-
1979
- 1979-10-22 YU YU02563/79A patent/YU256379A/xx unknown
- 1979-10-22 YU YU02564/79A patent/YU256479A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES332858A1 (es) | 1967-12-01 |
| GB1122604A (en) | 1968-08-07 |
| FI48739B (en, 2012) | 1974-09-02 |
| ES332860A1 (es) | 1967-12-01 |
| ES332861A1 (es) | 1967-12-01 |
| YU256379A (en) | 1983-02-28 |
| IL26768A (en) | 1970-09-17 |
| YU36726B (en) | 1984-08-31 |
| DE1695095A1 (de) | 1970-08-20 |
| SE346540B (en, 2012) | 1972-07-10 |
| ES332859A1 (es) | 1967-12-01 |
| YU203566A (en) | 1982-02-25 |
| FR6874M (en, 2012) | 1969-04-14 |
| BE689020A (en, 2012) | 1967-04-28 |
| DK121170B (da) | 1971-09-20 |
| DE1695095C3 (de) | 1974-05-02 |
| BR6684131D0 (pt) | 1973-12-26 |
| NL6615305A (en, 2012) | 1967-05-02 |
| DE1695095B2 (de) | 1973-09-06 |
| YU256479A (en) | 1983-01-21 |
| AT263769B (de) | 1968-08-12 |
| CH459216A (de) | 1968-07-15 |
| US3746717A (en) | 1973-07-17 |
| AT267523B (de) | 1969-01-10 |
| FI48739C (fi) | 1974-12-10 |
| NL149798B (nl) | 1976-06-15 |
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