FI63394C - Analogifoerfarande foer framstaellning av kemoterapeutiskt anvaendbara heteroarylfoereningar - Google Patents
Analogifoerfarande foer framstaellning av kemoterapeutiskt anvaendbara heteroarylfoereningar Download PDFInfo
- Publication number
- FI63394C FI63394C FI761585A FI761585A FI63394C FI 63394 C FI63394 C FI 63394C FI 761585 A FI761585 A FI 761585A FI 761585 A FI761585 A FI 761585A FI 63394 C FI63394 C FI 63394C
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- FI
- Finland
- Prior art keywords
- methyl
- alkyl
- mol
- cycloalkyl
- substituted
- Prior art date
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- 230000001225 therapeutic effect Effects 0.000 title description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 31
- 238000000034 method Methods 0.000 claims description 23
- 125000001072 heteroaryl group Chemical group 0.000 claims description 12
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical group 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 125000004520 1,3,4-thiadiazolyl group Chemical group 0.000 claims description 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
- 125000004442 acylamino group Chemical group 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 2
- 125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 claims 2
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims 1
- 150000001721 carbon Chemical group 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 52
- 150000001875 compounds Chemical class 0.000 description 34
- 239000000243 solution Substances 0.000 description 31
- -1 phenyl-substituted 1,2,4-oxadiazolyl Chemical group 0.000 description 30
- 238000004458 analytical method Methods 0.000 description 29
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
- 239000000203 mixture Substances 0.000 description 20
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 16
- 239000007787 solid Substances 0.000 description 16
- 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
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 239000003921 oil Substances 0.000 description 10
- 239000003208 petroleum Substances 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 8
- 235000019341 magnesium sulphate Nutrition 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 7
- 239000000460 chlorine Substances 0.000 description 7
- 238000001816 cooling Methods 0.000 description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 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
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 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
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 230000010933 acylation Effects 0.000 description 3
- 238000005917 acylation reaction Methods 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 239000012279 sodium borohydride Substances 0.000 description 3
- 229910000033 sodium borohydride Inorganic materials 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 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
- 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 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 2
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 2
- HMPUHXCGUHDVBI-UHFFFAOYSA-N 5-methyl-1,3,4-thiadiazol-2-amine Chemical compound CC1=NN=C(N)S1 HMPUHXCGUHDVBI-UHFFFAOYSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- 208000001718 Immediate Hypersensitivity Diseases 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 206010045240 Type I hypersensitivity Diseases 0.000 description 2
- 208000010216 atopic IgE responsiveness Diseases 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 239000012230 colorless oil Substances 0.000 description 2
- ZOOSILUVXHVRJE-UHFFFAOYSA-N cyclopropanecarbonyl chloride Chemical compound ClC(=O)C1CC1 ZOOSILUVXHVRJE-UHFFFAOYSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- LSACYLWPPQLVSM-UHFFFAOYSA-N isobutyric acid anhydride Chemical compound CC(C)C(=O)OC(=O)C(C)C LSACYLWPPQLVSM-UHFFFAOYSA-N 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000012280 lithium aluminium hydride Substances 0.000 description 2
- 239000007937 lozenge Substances 0.000 description 2
- 150000004866 oxadiazoles Chemical class 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000003786 synthesis reaction 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
- 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
- 125000004516 1,2,4-thiadiazol-5-yl group Chemical group S1N=CN=C1* 0.000 description 1
- YGTAZGSLCXNBQL-UHFFFAOYSA-N 1,2,4-thiadiazole Chemical class C=1N=CSN=1 YGTAZGSLCXNBQL-UHFFFAOYSA-N 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
- RQSCFNPNNLWQBJ-UHFFFAOYSA-N 2-methyl-1,3,4-thiadiazole Chemical compound CC1=NN=CS1 RQSCFNPNNLWQBJ-UHFFFAOYSA-N 0.000 description 1
- HWDWGFXCUSPGLA-UHFFFAOYSA-N 2-methyl-n-(5-methyl-1,3,4-oxadiazol-2-yl)-n-prop-2-enylpropanamide Chemical compound CC(C)C(=O)N(CC=C)C1=NN=C(C)O1 HWDWGFXCUSPGLA-UHFFFAOYSA-N 0.000 description 1
- UNQGCISQMCVIDO-UHFFFAOYSA-N 2-methyl-n-(5-methyl-1,3,4-thiadiazol-2-yl)propanamide Chemical compound CC(C)C(=O)NC1=NN=C(C)S1 UNQGCISQMCVIDO-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- KMZPYHWTYNCMMW-UHFFFAOYSA-N 3-methyl-n-propan-2-yl-1,2,4-oxadiazol-5-amine Chemical compound CC(C)NC1=NC(C)=NO1 KMZPYHWTYNCMMW-UHFFFAOYSA-N 0.000 description 1
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 description 1
- ILTLLMVRPBXCSX-UHFFFAOYSA-N 5-chloro-3-methyl-1,2,4-thiadiazole Chemical compound CC1=NSC(Cl)=N1 ILTLLMVRPBXCSX-UHFFFAOYSA-N 0.000 description 1
- OIMFGDHPGDUQKS-UHFFFAOYSA-N 5-methyl-n-propyl-1,3,4-oxadiazol-2-amine Chemical compound CCCNC1=NN=C(C)O1 OIMFGDHPGDUQKS-UHFFFAOYSA-N 0.000 description 1
- BKFKFGIPEUEPRV-UHFFFAOYSA-N 5-phenyl-5-(trichloromethyl)-2H-1,2,4-oxadiazole Chemical compound C1(=CC=CC=C1)C1(N=CNO1)C(Cl)(Cl)Cl BKFKFGIPEUEPRV-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
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZELQKDFESOKHGY-UHFFFAOYSA-N CC1(N=CNO1)N(C(C(C)C1=CC=CC=C1)=O)CC1=CC=CC=C1 Chemical compound CC1(N=CNO1)N(C(C(C)C1=CC=CC=C1)=O)CC1=CC=CC=C1 ZELQKDFESOKHGY-UHFFFAOYSA-N 0.000 description 1
- LCHAPQUPWHSYPT-UHFFFAOYSA-O CCCCCC(N[S+](C1N)C(C)=NN1C1=NN=C(C)S1)=O Chemical compound CCCCCC(N[S+](C1N)C(C)=NN1C1=NN=C(C)S1)=O LCHAPQUPWHSYPT-UHFFFAOYSA-O 0.000 description 1
- 241000320892 Clerodendrum phlomidis Species 0.000 description 1
- 241001302806 Helogenes Species 0.000 description 1
- OVSBPDCFHCXOBT-UHFFFAOYSA-N N-heptyl-5-methyl-1,3,4-thiadiazol-2-amine Chemical compound CCCCCCCNC1=NN=C(C)S1 OVSBPDCFHCXOBT-UHFFFAOYSA-N 0.000 description 1
- 241001315609 Pittosporum crassifolium Species 0.000 description 1
- 235000017284 Pometia pinnata Nutrition 0.000 description 1
- 240000009305 Pometia pinnata Species 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 241000630524 Taractes rubescens Species 0.000 description 1
- OFLXLNCGODUUOT-UHFFFAOYSA-N acetohydrazide Chemical compound C\C(O)=N\N OFLXLNCGODUUOT-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- HXBPYFMVGFDZFT-UHFFFAOYSA-N allyl isocyanate Chemical compound C=CCN=C=O HXBPYFMVGFDZFT-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- 210000003323 beak Anatomy 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Chemical group 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 description 1
- YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000000973 chemotherapeutic effect Effects 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- JFWMYCVMQSLLOO-UHFFFAOYSA-N cyclobutanecarbonyl chloride Chemical compound ClC(=O)C1CCC1 JFWMYCVMQSLLOO-UHFFFAOYSA-N 0.000 description 1
- RVOJTCZRIKWHDX-UHFFFAOYSA-N cyclohexanecarbonyl chloride Chemical compound ClC(=O)C1CCCCC1 RVOJTCZRIKWHDX-UHFFFAOYSA-N 0.000 description 1
- XRLDSWLMHUQECH-UHFFFAOYSA-N cyclopentanecarboxamide Chemical compound NC(=O)C1CCCC1 XRLDSWLMHUQECH-UHFFFAOYSA-N 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- WCQOBLXWLRDEQA-UHFFFAOYSA-N ethanimidamide;hydrochloride Chemical compound Cl.CC(N)=N WCQOBLXWLRDEQA-UHFFFAOYSA-N 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
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- 150000004820 halides Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- AEDIXYWIVPYNBI-UHFFFAOYSA-N heptanamide Chemical compound CCCCCCC(N)=O AEDIXYWIVPYNBI-UHFFFAOYSA-N 0.000 description 1
- PKHMTIRCAFTBDS-UHFFFAOYSA-N hexanoyl hexanoate Chemical compound CCCCCC(=O)OC(=O)CCCCC PKHMTIRCAFTBDS-UHFFFAOYSA-N 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 238000001361 intraarterial administration Methods 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- PTJCFEUUZZUUMB-UHFFFAOYSA-N n-(3-methyl-1,2,4-oxadiazol-5-yl)-n-[(4-methylphenyl)methyl]cyclopropanecarboxamide Chemical compound CC1=NOC(N(CC=2C=CC(C)=CC=2)C(=O)C2CC2)=N1 PTJCFEUUZZUUMB-UHFFFAOYSA-N 0.000 description 1
- GUQIGVLTJANONH-UHFFFAOYSA-N n-(5-methyl-1,3,4-oxadiazol-2-yl)-n-propylcyclobutanecarboxamide Chemical compound N=1N=C(C)OC=1N(CCC)C(=O)C1CCC1 GUQIGVLTJANONH-UHFFFAOYSA-N 0.000 description 1
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- QAYBESKDDYOSKG-UHFFFAOYSA-N n-benzyl-n-(5-methyl-1,3,4-thiadiazol-2-yl)-2-phenylacetamide Chemical compound S1C(C)=NN=C1N(C(=O)CC=1C=CC=CC=1)CC1=CC=CC=C1 QAYBESKDDYOSKG-UHFFFAOYSA-N 0.000 description 1
- OWLACUCANLMVRL-UHFFFAOYSA-N n-butyl-2-methyl-n-(3-methyl-1,2,4-oxadiazol-5-yl)propanamide Chemical compound CCCCN(C(=O)C(C)C)C1=NC(C)=NO1 OWLACUCANLMVRL-UHFFFAOYSA-N 0.000 description 1
- RJINNOAICWYHPS-UHFFFAOYSA-N n-butyl-3-methyl-1,2,4-thiadiazol-5-amine Chemical compound CCCCNC1=NC(C)=NS1 RJINNOAICWYHPS-UHFFFAOYSA-N 0.000 description 1
- UVXJXOKGEPCQBY-UHFFFAOYSA-N n-butyl-4-methoxy-n-(3-methyl-1,2,4-oxadiazol-5-yl)benzamide Chemical compound N=1C(C)=NOC=1N(CCCC)C(=O)C1=CC=C(OC)C=C1 UVXJXOKGEPCQBY-UHFFFAOYSA-N 0.000 description 1
- HGMZBBTZYCNURX-UHFFFAOYSA-N n-butyl-n-(3-methyl-1,2,4-thiadiazol-5-yl)cyclopropanecarboxamide Chemical compound N=1C(C)=NSC=1N(CCCC)C(=O)C1CC1 HGMZBBTZYCNURX-UHFFFAOYSA-N 0.000 description 1
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- WWCRDCXPJOVHNE-UHFFFAOYSA-N n-hexyl-n-(3-methyl-1,2,4-oxadiazol-5-yl)cyclopentanecarboxamide Chemical compound N=1C(C)=NOC=1N(CCCCCC)C(=O)C1CCCC1 WWCRDCXPJOVHNE-UHFFFAOYSA-N 0.000 description 1
- FHLASMUMHFWRKE-UHFFFAOYSA-N n-hexyl-n-(3-methyl-1,2,4-thiadiazol-5-yl)acetamide Chemical compound CCCCCCN(C(C)=O)C1=NC(C)=NS1 FHLASMUMHFWRKE-UHFFFAOYSA-N 0.000 description 1
- FIOGTEHETWKJJI-UHFFFAOYSA-N n-methyl-1,2,4-thiadiazol-5-amine Chemical compound CNC1=NC=NS1 FIOGTEHETWKJJI-UHFFFAOYSA-N 0.000 description 1
- DNRPANYGQOCDEW-UHFFFAOYSA-N n-methyl-n-(5-methyl-1,3,4-thiadiazol-2-yl)benzamide Chemical compound N=1N=C(C)SC=1N(C)C(=O)C1=CC=CC=C1 DNRPANYGQOCDEW-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
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- 239000012044 organic layer Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 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
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000012058 sterile packaged powder Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- ZCPSWAFANXCCOT-UHFFFAOYSA-N trichloromethanesulfonyl chloride Chemical compound ClC(Cl)(Cl)S(Cl)(=O)=O ZCPSWAFANXCCOT-UHFFFAOYSA-N 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)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB24224/75A GB1551735A (en) | 1975-06-05 | 1975-06-05 | Acylated aminothiazoles and aminooxadiazoles |
| GB2422475 | 1975-06-05 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI761585A7 FI761585A7 (enrdf_load_stackoverflow) | 1976-12-06 |
| FI63394B FI63394B (fi) | 1983-02-28 |
| FI63394C true FI63394C (fi) | 1983-06-10 |
Family
ID=10208350
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI761585A FI63394C (fi) | 1975-06-05 | 1976-06-04 | Analogifoerfarande foer framstaellning av kemoterapeutiskt anvaendbara heteroarylfoereningar |
Country Status (34)
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2834945A1 (de) * | 1977-08-15 | 1979-03-01 | Lilly Co Eli | Thiadiazolylbenzamide, verfahren zu ihrer herstellung und sie enthaltende insektizide mittel |
| DE2805756A1 (de) * | 1978-02-10 | 1979-08-16 | Bayer Ag | N-azolylalkyl-aniline sowie verfahren zu ihrer herstellung |
| DE2805757A1 (de) * | 1978-02-10 | 1979-08-16 | Bayer Ag | N-azolylalkyl-halogenacetanilide, verfahren zu ihrer herstellung sowie ihre verwendung als herbizide |
| US4285959A (en) * | 1979-05-18 | 1981-08-25 | Ciba-Geigy Corporation | 3-(N-1,3,4-Thiadiazolyl-2)-aminoalkyl-alkyl-acrylates and use thereof as bactericides |
| 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 . |
| DE3120804A1 (de) | 1981-05-25 | 1982-12-16 | Basf Ag, 6700 Ludwigshafen | N-substituierte 2-methylnaphthylamide, verfahren zu ihrer herstellung und ihre verwendung zur bekaempfung von pilzen |
| US4874864A (en) * | 1988-05-24 | 1989-10-17 | Pfizer Inc. | Benzamide protease inhibitors |
| AU2010601A (en) * | 1999-12-16 | 2001-07-03 | Novartis Ag | Organic compounds |
| TW200503994A (en) * | 2003-01-24 | 2005-02-01 | Novartis Ag | Organic compounds |
| 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)
| 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 NZ NZ181011A patent/NZ181011A/xx unknown
- 1976-05-31 IE IE1148/76A patent/IE43474B1/en unknown
- 1976-05-31 FR FR7616338A patent/FR2313049A1/fr active Granted
- 1976-05-31 IL IL49692A patent/IL49692A/xx unknown
- 1976-05-31 CA CA253,755A patent/CA1085860A/en not_active Expired
- 1976-06-01 GR GR50868A patent/GR60380B/el unknown
- 1976-06-01 AR AR263474A patent/AR217240A1/es active
- 1976-06-01 CH CH685576A patent/CH612427A5/xx not_active IP Right Cessation
- 1976-06-01 ZA ZA00763209A patent/ZA763209B/xx unknown
- 1976-06-02 DK DK243276A patent/DK243276A/da not_active Application Discontinuation
- 1976-06-02 LU LU75070A patent/LU75070A1/xx unknown
- 1976-06-02 SE SE7606226A patent/SE428561B/xx unknown
- 1976-06-03 PT PT65182A patent/PT65182B/pt unknown
- 1976-06-03 YU YU01371/76A patent/YU137176A/xx unknown
- 1976-06-03 CS CS763692A patent/CS200494B2/cs unknown
- 1976-06-03 BE BE6045539A patent/BE842579A/xx not_active IP Right Cessation
- 1976-06-03 HU HU76LI293A patent/HU174191B/hu unknown
- 1976-06-03 AU AU14619/76A patent/AU503150B2/en not_active Expired
- 1976-06-04 FI FI761585A patent/FI63394C/fi not_active IP Right Cessation
- 1976-06-04 ES ES448590A patent/ES448590A1/es not_active Expired
- 1976-06-04 JP JP51066027A patent/JPS51146468A/ja active Pending
- 1976-06-04 PH PH18535A patent/PH16077A/en unknown
- 1976-06-04 DD DD193198A patent/DD125075A5/xx unknown
- 1976-06-04 SU SU762366751A patent/SU639451A3/ru active
- 1976-06-04 MX MX000265U patent/MX3483E/es unknown
- 1976-06-04 PL PL1976190132A patent/PL103004B1/pl unknown
- 1976-06-04 BG BG033366A patent/BG27359A3/xx unknown
- 1976-06-04 AT AT412276A patent/AT346843B/de not_active IP Right Cessation
- 1976-06-04 DE DE19762625285 patent/DE2625285A1/de not_active Ceased
- 1976-06-04 NO NO761913A patent/NO144346C/no unknown
- 1976-06-05 EG EG76334A patent/EG12226A/xx active
- 1976-06-05 OA OA55843A patent/OA05346A/xx unknown
- 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
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: LILLY INDUSTRIES LTD |