CA1180705A - Thiazol-2-yl-oxamic acid derivatives, their preparation and therapeutic agents containing these compounds - Google Patents
Thiazol-2-yl-oxamic acid derivatives, their preparation and therapeutic agents containing these compoundsInfo
- Publication number
- CA1180705A CA1180705A CA000381695A CA381695A CA1180705A CA 1180705 A CA1180705 A CA 1180705A CA 000381695 A CA000381695 A CA 000381695A CA 381695 A CA381695 A CA 381695A CA 1180705 A CA1180705 A CA 1180705A
- Authority
- CA
- Canada
- Prior art keywords
- formula
- carbon atoms
- alkyl
- radical
- phenyl
- Prior art date
- 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.)
- Expired
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 56
- 238000002360 preparation method Methods 0.000 title claims abstract description 12
- 239000003814 drug Substances 0.000 title abstract description 7
- 229940124597 therapeutic agent Drugs 0.000 title abstract description 5
- OPYBRLFGZHVSOI-UHFFFAOYSA-N 2-oxo-2-(1,3-thiazol-2-ylamino)acetic acid Chemical class OC(=O)C(=O)NC1=NC=CS1 OPYBRLFGZHVSOI-UHFFFAOYSA-N 0.000 title description 3
- -1 2-substituted thiazol-2-yl-oxamic acid esters Chemical class 0.000 claims abstract description 78
- 238000000034 method Methods 0.000 claims abstract description 37
- 125000004432 carbon atom Chemical group C* 0.000 claims description 49
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 42
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 40
- 125000000217 alkyl group Chemical group 0.000 claims description 35
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 19
- SOWBFZRMHSNYGE-UHFFFAOYSA-N oxamic acid Chemical compound NC(=O)C(O)=O SOWBFZRMHSNYGE-UHFFFAOYSA-N 0.000 claims description 17
- 239000002253 acid Substances 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 7
- RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical compound NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical group 0.000 claims description 6
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 claims description 5
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 5
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- DCANGVYZWYRVOB-UHFFFAOYSA-N 2-amino-2-oxoacetyl chloride Chemical compound NC(=O)C(Cl)=O DCANGVYZWYRVOB-UHFFFAOYSA-N 0.000 claims description 4
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 4
- ZOOQXNXFZXSKMS-UHFFFAOYSA-N 2-ethoxyethyl 2-oxo-2-[(4-phenyl-1,3-thiazol-2-yl)amino]acetate Chemical compound S1C(NC(=O)C(=O)OCCOCC)=NC(C=2C=CC=CC=2)=C1 ZOOQXNXFZXSKMS-UHFFFAOYSA-N 0.000 claims description 3
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000005518 carboxamido group Chemical group 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000002757 morpholinyl group Chemical group 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 3
- 125000005936 piperidyl group Chemical group 0.000 claims description 3
- MOZWOXRVGUTEIG-UHFFFAOYSA-N 2-[(2-amino-4-phenyl-1,3-thiazol-5-yl)amino]-2-oxoacetic acid Chemical compound S1C(N)=NC(C=2C=CC=CC=2)=C1NC(=O)C(O)=O MOZWOXRVGUTEIG-UHFFFAOYSA-N 0.000 claims description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 2
- 239000008096 xylene Substances 0.000 claims description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 2
- 230000000172 allergic effect Effects 0.000 abstract description 4
- 208000010668 atopic eczema Diseases 0.000 abstract description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 4
- 235000013350 formula milk Nutrition 0.000 description 44
- 238000002844 melting Methods 0.000 description 23
- 230000008018 melting Effects 0.000 description 23
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Substances ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 22
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
- 238000002425 crystallisation Methods 0.000 description 17
- 230000008025 crystallization Effects 0.000 description 17
- 150000003254 radicals Chemical group 0.000 description 17
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 235000019441 ethanol Nutrition 0.000 description 15
- 239000000203 mixture Substances 0.000 description 15
- 239000000047 product Substances 0.000 description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- 230000003266 anti-allergic effect Effects 0.000 description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 241000700159 Rattus Species 0.000 description 6
- 238000009472 formulation Methods 0.000 description 5
- 229940086542 triethylamine Drugs 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- OWRNLGZKEZSHGO-UHFFFAOYSA-N 2-[2-[2-[2-[2-[2-(2-hydroxypropoxy)propoxy]propoxy]propoxy]propoxy]propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)COC(C)COC(C)COC(C)COC(C)CO OWRNLGZKEZSHGO-UHFFFAOYSA-N 0.000 description 4
- ZZEANNAZZVVPKU-UHFFFAOYSA-N 2-[2-[2-[2-[2-[2-[2-(2-hydroxypropoxy)propoxy]propoxy]propoxy]propoxy]propoxy]propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)COC(C)COC(C)COC(C)COC(C)COC(C)CO ZZEANNAZZVVPKU-UHFFFAOYSA-N 0.000 description 4
- MCVKSYYBBHNAFN-UHFFFAOYSA-N 2-[2-[2-[2-[2-[2-[2-[2-[2-(2-hydroxypropoxy)propoxy]propoxy]propoxy]propoxy]propoxy]propoxy]propoxy]propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)COC(C)COC(C)COC(C)COC(C)COC(C)COC(C)COC(C)CO MCVKSYYBBHNAFN-UHFFFAOYSA-N 0.000 description 4
- XHFUWPYJAUFIDN-UHFFFAOYSA-N 2-oxo-2-[(4-phenyl-1,3-thiazol-2-yl)amino]acetic acid Chemical compound S1C(NC(=O)C(=O)O)=NC(C=2C=CC=CC=2)=C1 XHFUWPYJAUFIDN-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 3
- DXVLAUMXGHQKAV-UHFFFAOYSA-N 2-[2-[2-[2-[2-[2-[2-[2-(2-hydroxypropoxy)propoxy]propoxy]propoxy]propoxy]propoxy]propoxy]propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)COC(C)COC(C)COC(C)COC(C)COC(C)COC(C)CO DXVLAUMXGHQKAV-UHFFFAOYSA-N 0.000 description 3
- WGKYSFRFMQHMOF-UHFFFAOYSA-N 3-bromo-5-methylpyridine-2-carbonitrile Chemical compound CC1=CN=C(C#N)C(Br)=C1 WGKYSFRFMQHMOF-UHFFFAOYSA-N 0.000 description 3
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 3
- PYSJLPAOBIGQPK-UHFFFAOYSA-N 4-phenyl-1,3-thiazol-2-amine Chemical compound S1C(N)=NC(C=2C=CC=CC=2)=C1 PYSJLPAOBIGQPK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- QVHMSMOUDQXMRS-UHFFFAOYSA-N PPG n4 Chemical compound CC(O)COC(C)COC(C)COC(C)CO QVHMSMOUDQXMRS-UHFFFAOYSA-N 0.000 description 3
- 239000000370 acceptor Substances 0.000 description 3
- 239000003610 charcoal Substances 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 3
- 208000035475 disorder Diseases 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 238000007912 intraperitoneal administration Methods 0.000 description 3
- 229940073584 methylene chloride Drugs 0.000 description 3
- 238000005303 weighing Methods 0.000 description 3
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical class CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 2
- AQRQHYITOOVBTO-UHFFFAOYSA-N 2-[2-[2-[2-(2-hydroxypropoxy)propoxy]propoxy]propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)COC(C)COC(C)CO AQRQHYITOOVBTO-UHFFFAOYSA-N 0.000 description 2
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 2
- GUGQQGROXHPINL-UHFFFAOYSA-N 2-oxobutanoyl chloride Chemical compound CCC(=O)C(Cl)=O GUGQQGROXHPINL-UHFFFAOYSA-N 0.000 description 2
- 125000005809 3,4,5-trimethoxyphenyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 2
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 2
- 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 description 2
- QKYORNXSXAOYPV-UHFFFAOYSA-N 4-(2,4,6-trimethylphenyl)-1,3-thiazol-2-amine Chemical compound CC1=CC(C)=CC(C)=C1C1=CSC(N)=N1 QKYORNXSXAOYPV-UHFFFAOYSA-N 0.000 description 2
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 206010002198 Anaphylactic reaction Diseases 0.000 description 2
- COXVTLYNGOIATD-HVMBLDELSA-N CC1=C(C=CC(=C1)C1=CC(C)=C(C=C1)\N=N\C1=C(O)C2=C(N)C(=CC(=C2C=C1)S(O)(=O)=O)S(O)(=O)=O)\N=N\C1=CC=C2C(=CC(=C(N)C2=C1O)S(O)(=O)=O)S(O)(=O)=O Chemical compound CC1=C(C=CC(=C1)C1=CC(C)=C(C=C1)\N=N\C1=C(O)C2=C(N)C(=CC(=C2C=C1)S(O)(=O)=O)S(O)(=O)=O)\N=N\C1=CC=C2C(=CC(=C(N)C2=C1O)S(O)(=O)=O)S(O)(=O)=O COXVTLYNGOIATD-HVMBLDELSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- 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 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 238000011785 NMRI mouse Methods 0.000 description 2
- 108010058846 Ovalbumin Proteins 0.000 description 2
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Natural products OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000007059 acute toxicity Effects 0.000 description 2
- 231100000403 acute toxicity Toxicity 0.000 description 2
- 230000036783 anaphylactic response Effects 0.000 description 2
- 208000003455 anaphylaxis Diseases 0.000 description 2
- 239000000043 antiallergic agent Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- DTPCFIHYWYONMD-UHFFFAOYSA-N decaethylene glycol Chemical compound OCCOCCOCCOCCOCCOCCOCCOCCOCCOCCO DTPCFIHYWYONMD-UHFFFAOYSA-N 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 229960003699 evans blue Drugs 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 229940090044 injection Drugs 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- JIQNWFBLYKVZFY-UHFFFAOYSA-N methoxycyclohexatriene Chemical compound COC1=C[C]=CC=C1 JIQNWFBLYKVZFY-UHFFFAOYSA-N 0.000 description 2
- 229920000847 nonoxynol Polymers 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
- 229940092253 ovalbumin Drugs 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 2
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 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
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- CUVLMZNMSPJDON-UHFFFAOYSA-N 1-(1-butoxypropan-2-yloxy)propan-2-ol Chemical compound CCCCOCC(C)OCC(C)O CUVLMZNMSPJDON-UHFFFAOYSA-N 0.000 description 1
- QWOZZTWBWQMEPD-UHFFFAOYSA-N 1-(2-ethoxypropoxy)propan-2-ol Chemical compound CCOC(C)COCC(C)O QWOZZTWBWQMEPD-UHFFFAOYSA-N 0.000 description 1
- RWNUSVWFHDHRCJ-UHFFFAOYSA-N 1-butoxypropan-2-ol Chemical compound CCCCOCC(C)O RWNUSVWFHDHRCJ-UHFFFAOYSA-N 0.000 description 1
- JOLQKTGDSGKSKJ-UHFFFAOYSA-N 1-ethoxypropan-2-ol Chemical compound CCOCC(C)O JOLQKTGDSGKSKJ-UHFFFAOYSA-N 0.000 description 1
- NUTVORGGYDQIDD-UHFFFAOYSA-N 1-ethylsulfanylethanol Chemical compound CCSC(C)O NUTVORGGYDQIDD-UHFFFAOYSA-N 0.000 description 1
- JLPULHDHAOZNQI-ZTIMHPMXSA-N 1-hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC JLPULHDHAOZNQI-ZTIMHPMXSA-N 0.000 description 1
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 1
- 125000005808 2,4,6-trimethoxyphenyl group Chemical group [H][#6]-1=[#6](-[#8]C([H])([H])[H])-[#6](-*)=[#6](-[#8]C([H])([H])[H])-[#6]([H])=[#6]-1-[#8]C([H])([H])[H] 0.000 description 1
- BEVWMRQFVUOPJT-UHFFFAOYSA-N 2,4-dimethyl-1,3-thiazole-5-carboxamide Chemical compound CC1=NC(C)=C(C(N)=O)S1 BEVWMRQFVUOPJT-UHFFFAOYSA-N 0.000 description 1
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 1
- SLNYBUIEAMRFSZ-UHFFFAOYSA-N 2-(2-{2-[2-(2-methoxy-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethanol Chemical compound COCCOCCOCCOCCOCCO SLNYBUIEAMRFSZ-UHFFFAOYSA-N 0.000 description 1
- CUDPPTPIUWYGFI-UHFFFAOYSA-N 2-(2-{2-[2-(2-{2-[2-(2-ethoxy-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethanol, polyethyleneglycol peg400 Chemical compound CCOCCOCCOCCOCCOCCOCCOCCOCCO CUDPPTPIUWYGFI-UHFFFAOYSA-N 0.000 description 1
- COBPKKZHLDDMTB-UHFFFAOYSA-N 2-[2-(2-butoxyethoxy)ethoxy]ethanol Chemical compound CCCCOCCOCCOCCO COBPKKZHLDDMTB-UHFFFAOYSA-N 0.000 description 1
- JDSQBDGCMUXRBM-UHFFFAOYSA-N 2-[2-(2-butoxypropoxy)propoxy]propan-1-ol Chemical compound CCCCOC(C)COC(C)COC(C)CO JDSQBDGCMUXRBM-UHFFFAOYSA-N 0.000 description 1
- FMVOPJLFZGSYOS-UHFFFAOYSA-N 2-[2-(2-ethoxypropoxy)propoxy]propan-1-ol Chemical compound CCOC(C)COC(C)COC(C)CO FMVOPJLFZGSYOS-UHFFFAOYSA-N 0.000 description 1
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 description 1
- WAEVWDZKMBQDEJ-UHFFFAOYSA-N 2-[2-(2-methoxypropoxy)propoxy]propan-1-ol Chemical compound COC(C)COC(C)COC(C)CO WAEVWDZKMBQDEJ-UHFFFAOYSA-N 0.000 description 1
- MXVMODFDROLTFD-UHFFFAOYSA-N 2-[2-[2-(2-butoxyethoxy)ethoxy]ethoxy]ethanol Chemical compound CCCCOCCOCCOCCOCCO MXVMODFDROLTFD-UHFFFAOYSA-N 0.000 description 1
- GTAKOUPXIUWZIA-UHFFFAOYSA-N 2-[2-[2-(2-ethoxyethoxy)ethoxy]ethoxy]ethanol Chemical compound CCOCCOCCOCCOCCO GTAKOUPXIUWZIA-UHFFFAOYSA-N 0.000 description 1
- NREVKVJUSKPCFL-UHFFFAOYSA-N 2-[2-[2-(2-methoxypropoxy)propoxy]propoxy]propan-1-ol Chemical compound COC(C)COC(C)COC(C)COC(C)CO NREVKVJUSKPCFL-UHFFFAOYSA-N 0.000 description 1
- AZYICGMHYYVGBY-UHFFFAOYSA-N 2-[2-[2-[2-(2-butoxyethoxy)ethoxy]ethoxy]ethoxy]ethanol Chemical compound CCCCOCCOCCOCCOCCOCCO AZYICGMHYYVGBY-UHFFFAOYSA-N 0.000 description 1
- QYYPGMDWEMYVBT-UHFFFAOYSA-N 2-[2-[2-[2-(2-butoxypropoxy)propoxy]propoxy]propoxy]propan-1-ol Chemical compound CCCCOC(C)COC(C)COC(C)COC(C)COC(C)CO QYYPGMDWEMYVBT-UHFFFAOYSA-N 0.000 description 1
- CUMNTCCDMXWANM-UHFFFAOYSA-N 2-[2-[2-[2-(2-methoxypropoxy)propoxy]propoxy]propoxy]propan-1-ol Chemical compound COC(C)COC(C)COC(C)COC(C)COC(C)CO CUMNTCCDMXWANM-UHFFFAOYSA-N 0.000 description 1
- LBFDMOHFDLVACT-UHFFFAOYSA-N 2-[2-[2-[2-[2-(2-butoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethanol Chemical compound CCCCOCCOCCOCCOCCOCCOCCO LBFDMOHFDLVACT-UHFFFAOYSA-N 0.000 description 1
- XRKKRXMLKMRERW-UHFFFAOYSA-N 2-[2-[2-[2-[2-(2-butoxypropoxy)propoxy]propoxy]propoxy]propoxy]propan-1-ol Chemical compound CCCCOC(C)COC(C)COC(C)COC(C)COC(C)COC(C)CO XRKKRXMLKMRERW-UHFFFAOYSA-N 0.000 description 1
- UKXKPKBTMYNOFS-UHFFFAOYSA-N 2-[2-[2-[2-[2-(2-ethoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethanol Chemical compound CCOCCOCCOCCOCCOCCOCCO UKXKPKBTMYNOFS-UHFFFAOYSA-N 0.000 description 1
- WXOFVHLGWKHIDD-UHFFFAOYSA-N 2-[2-[2-[2-[2-(2-ethoxypropoxy)propoxy]propoxy]propoxy]propoxy]propan-1-ol Chemical compound CCOC(C)COC(C)COC(C)COC(C)COC(C)COC(C)CO WXOFVHLGWKHIDD-UHFFFAOYSA-N 0.000 description 1
- UDOJNGPPRYJMKR-UHFFFAOYSA-N 2-[2-[2-[2-[2-(2-hydroxypropoxy)propoxy]propoxy]propoxy]propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)COC(C)COC(C)COC(C)CO UDOJNGPPRYJMKR-UHFFFAOYSA-N 0.000 description 1
- NJGQZSXQBSFIRB-UHFFFAOYSA-N 2-[2-[2-[2-[2-(2-methoxypropoxy)propoxy]propoxy]propoxy]propoxy]propan-1-ol Chemical compound COC(C)COC(C)COC(C)COC(C)COC(C)COC(C)CO NJGQZSXQBSFIRB-UHFFFAOYSA-N 0.000 description 1
- QIBDLDQWDGOWTN-UHFFFAOYSA-N 2-[2-[2-[2-[2-[2-(2-butoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethanol Chemical compound CCCCOCCOCCOCCOCCOCCOCCOCCO QIBDLDQWDGOWTN-UHFFFAOYSA-N 0.000 description 1
- PJWQOENWHPEPKI-UHFFFAOYSA-N 2-[2-[2-[2-[2-[2-(2-ethoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethanol Chemical compound CCOCCOCCOCCOCCOCCOCCOCCO PJWQOENWHPEPKI-UHFFFAOYSA-N 0.000 description 1
- AGWKUHGLWHMYTG-UHFFFAOYSA-N 2-[2-[2-[2-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethanol Chemical compound COCCOCCOCCOCCOCCOCCOCCO AGWKUHGLWHMYTG-UHFFFAOYSA-N 0.000 description 1
- VGHRBQZMSNEHGX-UHFFFAOYSA-N 2-[2-[2-[2-[2-[2-[2-(2-butoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethanol Chemical compound CCCCOCCOCCOCCOCCOCCOCCOCCOCCO VGHRBQZMSNEHGX-UHFFFAOYSA-N 0.000 description 1
- SZGNWRSFHADOMY-UHFFFAOYSA-N 2-[2-[2-[2-[2-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethanol Chemical compound COCCOCCOCCOCCOCCOCCOCCOCCO SZGNWRSFHADOMY-UHFFFAOYSA-N 0.000 description 1
- XUIHSBSMRCNZOZ-UHFFFAOYSA-N 2-[2-[2-[2-[2-[2-[2-[2-[2-(2-ethoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethanol Chemical compound CCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCO XUIHSBSMRCNZOZ-UHFFFAOYSA-N 0.000 description 1
- YMBLPWKGRIGDBP-UHFFFAOYSA-N 2-[2-[2-[2-[2-[2-[2-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethanol Chemical compound COCCOCCOCCOCCOCCOCCOCCOCCOCCOCCO YMBLPWKGRIGDBP-UHFFFAOYSA-N 0.000 description 1
- MEFAMGAUYYVCSC-UHFFFAOYSA-N 2-[[4-(2,4-dihydroxyphenyl)-1,3-thiazol-2-yl]amino]-2-oxoacetic acid Chemical compound S1C(NC(=O)C(=O)O)=NC(C=2C(=CC(O)=CC=2)O)=C1 MEFAMGAUYYVCSC-UHFFFAOYSA-N 0.000 description 1
- HFDGOXJFYZFEMS-UHFFFAOYSA-N 2-[[4-(2,5-dimethoxyphenyl)-1,3-thiazol-2-yl]amino]-2-oxoacetic acid Chemical compound COC1=CC=C(OC)C(C=2N=C(NC(=O)C(O)=O)SC=2)=C1 HFDGOXJFYZFEMS-UHFFFAOYSA-N 0.000 description 1
- KLFZXGCUWMXUGW-UHFFFAOYSA-N 2-[[4-(2-ethoxyphenyl)-1,3-thiazol-2-yl]amino]-2-oxoacetic acid Chemical compound CCOC1=CC=CC=C1C1=CSC(NC(=O)C(O)=O)=N1 KLFZXGCUWMXUGW-UHFFFAOYSA-N 0.000 description 1
- MVJABZPHPZKKIL-UHFFFAOYSA-N 2-[[4-(2-hydroxy-4-methoxyphenyl)-1,3-thiazol-2-yl]amino]-2-oxoacetic acid Chemical compound OC1=CC(OC)=CC=C1C1=CSC(NC(=O)C(O)=O)=N1 MVJABZPHPZKKIL-UHFFFAOYSA-N 0.000 description 1
- BESVVKLRLZEKFY-UHFFFAOYSA-N 2-[[4-(2-hydroxyphenyl)-1,3-thiazol-2-yl]amino]-2-oxoacetic acid Chemical compound S1C(NC(=O)C(=O)O)=NC(C=2C(=CC=CC=2)O)=C1 BESVVKLRLZEKFY-UHFFFAOYSA-N 0.000 description 1
- CTISGDWSANJZIG-UHFFFAOYSA-N 2-[[4-(3,4-dimethoxyphenyl)-1,3-thiazol-2-yl]amino]-2-oxoacetic acid Chemical compound C1=C(OC)C(OC)=CC=C1C1=CSC(NC(=O)C(O)=O)=N1 CTISGDWSANJZIG-UHFFFAOYSA-N 0.000 description 1
- UDILYWUJOHMWFZ-UHFFFAOYSA-N 2-[[4-(3,5-dimethoxyphenyl)-1,3-thiazol-2-yl]amino]-2-oxoacetic acid Chemical compound COC1=CC(OC)=CC(C=2N=C(NC(=O)C(O)=O)SC=2)=C1 UDILYWUJOHMWFZ-UHFFFAOYSA-N 0.000 description 1
- APCOGOGCOPKLEA-UHFFFAOYSA-N 2-[[4-(3-hydroxyphenyl)-1,3-thiazol-2-yl]amino]-2-oxoacetic acid Chemical compound S1C(NC(=O)C(=O)O)=NC(C=2C=C(O)C=CC=2)=C1 APCOGOGCOPKLEA-UHFFFAOYSA-N 0.000 description 1
- DJZZHJGHDULMLW-UHFFFAOYSA-N 2-[[4-(4-ethoxyphenyl)-1,3-thiazol-2-yl]amino]-2-oxoacetic acid Chemical compound C1=CC(OCC)=CC=C1C1=CSC(NC(=O)C(O)=O)=N1 DJZZHJGHDULMLW-UHFFFAOYSA-N 0.000 description 1
- STKFNYHPGAKISI-UHFFFAOYSA-N 2-[[4-(4-hydroxy-3-methoxyphenyl)-1,3-thiazol-2-yl]amino]-2-oxoacetic acid Chemical compound C1=C(O)C(OC)=CC(C=2N=C(NC(=O)C(O)=O)SC=2)=C1 STKFNYHPGAKISI-UHFFFAOYSA-N 0.000 description 1
- FDXVHEDJSXWBHD-UHFFFAOYSA-N 2-[[4-(4-methoxyphenyl)-1,3-thiazol-2-yl]amino]-2-oxoacetic acid Chemical compound C1=CC(OC)=CC=C1C1=CSC(NC(=O)C(O)=O)=N1 FDXVHEDJSXWBHD-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- ANEYQYLJYLBVBN-UHFFFAOYSA-N 2-ethoxyethyl 2-[[4-(2,4-dimethoxyphenyl)-1,3-thiazol-2-yl]amino]-2-oxoacetate Chemical compound S1C(NC(=O)C(=O)OCCOCC)=NC(C=2C(=CC(OC)=CC=2)OC)=C1 ANEYQYLJYLBVBN-UHFFFAOYSA-N 0.000 description 1
- MVZBYARFOGIGPN-UHFFFAOYSA-N 2-ethoxyethyl 2-[[4-(2,5-dimethoxyphenyl)-1,3-thiazol-2-yl]amino]-2-oxoacetate Chemical compound S1C(NC(=O)C(=O)OCCOCC)=NC(C=2C(=CC=C(OC)C=2)OC)=C1 MVZBYARFOGIGPN-UHFFFAOYSA-N 0.000 description 1
- OJNVCEZZRUGANK-UHFFFAOYSA-N 2-ethoxyethyl 2-[[4-(4-methoxyphenyl)-1,3-thiazol-2-yl]amino]-2-oxoacetate Chemical compound S1C(NC(=O)C(=O)OCCOCC)=NC(C=2C=CC(OC)=CC=2)=C1 OJNVCEZZRUGANK-UHFFFAOYSA-N 0.000 description 1
- URHOEVBBDWOUQZ-UHFFFAOYSA-N 2-ethylsulfanylethyl 2-oxo-2-[(4-phenyl-1,3-thiazol-2-yl)amino]acetate Chemical compound S1C(NC(=O)C(=O)OCCSCC)=NC(C=2C=CC=CC=2)=C1 URHOEVBBDWOUQZ-UHFFFAOYSA-N 0.000 description 1
- ZSSSUXLAVXQWSM-UHFFFAOYSA-N 2-methoxyethyl 2-oxo-2-[(4-phenyl-1,3-thiazol-2-yl)amino]acetate Chemical compound S1C(NC(=O)C(=O)OCCOC)=NC(C=2C=CC=CC=2)=C1 ZSSSUXLAVXQWSM-UHFFFAOYSA-N 0.000 description 1
- QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 description 1
- WKWKCGKDMSXQEN-UHFFFAOYSA-N 2-phenoxyethyl 2-oxo-2-[(4-phenyl-1,3-thiazol-2-yl)amino]acetate Chemical compound C=1C=CC=CC=1OCCOC(=O)C(=O)NC(SC=1)=NC=1C1=CC=CC=C1 WKWKCGKDMSXQEN-UHFFFAOYSA-N 0.000 description 1
- NXZVNAKCBHOEIN-UHFFFAOYSA-N 2-phenylethyl 2-[[4-(4-methoxyphenyl)-1,3-thiazol-2-yl]amino]-2-oxoacetate Chemical compound C1=CC(OC)=CC=C1C1=CSC(NC(=O)C(=O)OCCC=2C=CC=CC=2)=N1 NXZVNAKCBHOEIN-UHFFFAOYSA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- IHVPVVBAWXXNFF-UHFFFAOYSA-N 2-phenylpropyl 2-oxo-2-[(4-phenyl-1,3-thiazol-2-yl)amino]acetate Chemical compound C=1C=CC=CC=1C(C)COC(=O)C(=O)NC(SC=1)=NC=1C1=CC=CC=C1 IHVPVVBAWXXNFF-UHFFFAOYSA-N 0.000 description 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- NJRFAMBTWHGSDE-UHFFFAOYSA-N 3,6,9,12,15-pentaoxaheptadecan-1-ol Chemical compound CCOCCOCCOCCOCCOCCO NJRFAMBTWHGSDE-UHFFFAOYSA-N 0.000 description 1
- QCAHUFWKIQLBNB-UHFFFAOYSA-N 3-(3-methoxypropoxy)propan-1-ol Chemical compound COCCCOCCCO QCAHUFWKIQLBNB-UHFFFAOYSA-N 0.000 description 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
- NRGCDEWBJMQJBX-UHFFFAOYSA-N 4-(2,4-dimethoxyphenyl)-1,3-thiazol-2-amine Chemical compound COC1=CC(OC)=CC=C1C1=CSC(N)=N1 NRGCDEWBJMQJBX-UHFFFAOYSA-N 0.000 description 1
- FXGVKHSZIMCUTR-UHFFFAOYSA-N 4-(2,5-dimethoxyphenyl)-1,3-thiazol-2-amine Chemical compound COC1=CC=C(OC)C(C=2N=C(N)SC=2)=C1 FXGVKHSZIMCUTR-UHFFFAOYSA-N 0.000 description 1
- YPVVEXKDPBRGIK-UHFFFAOYSA-N 4-(4-methoxyphenyl)-1,3-thiazol-2-amine Chemical compound C1=CC(OC)=CC=C1C1=CSC(N)=N1 YPVVEXKDPBRGIK-UHFFFAOYSA-N 0.000 description 1
- ABCNUVGFUGMTOA-UHFFFAOYSA-N 4-(4-tert-butylphenyl)-1,3-thiazol-2-amine Chemical compound C1=CC(C(C)(C)C)=CC=C1C1=CSC(N)=N1 ABCNUVGFUGMTOA-UHFFFAOYSA-N 0.000 description 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 244000215068 Acacia senegal Species 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
- 241000416162 Astragalus gummifer Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241000518994 Conta Species 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- 239000003109 Disodium ethylene diamine tetraacetate Substances 0.000 description 1
- ZGTMUACCHSMWAC-UHFFFAOYSA-L EDTA disodium salt (anhydrous) Chemical compound [Na+].[Na+].OC(=O)CN(CC([O-])=O)CCN(CC(O)=O)CC([O-])=O ZGTMUACCHSMWAC-UHFFFAOYSA-L 0.000 description 1
- 208000004262 Food Hypersensitivity Diseases 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- 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 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
- 241000699670 Mus sp. Species 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 206010039085 Rhinitis allergic Diseases 0.000 description 1
- 206010070834 Sensitisation Diseases 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 229920002472 Starch Polymers 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
- 239000000443 aerosol Substances 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 201000009961 allergic asthma Diseases 0.000 description 1
- 201000010105 allergic rhinitis Diseases 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229950003476 aminothiazole Drugs 0.000 description 1
- 239000000427 antigen Substances 0.000 description 1
- 102000036639 antigens Human genes 0.000 description 1
- 108091007433 antigens Proteins 0.000 description 1
- 239000008135 aqueous vehicle Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000012050 conventional carrier Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- JBRSGWMGMGXGBZ-UHFFFAOYSA-N cyclohexyl 2-oxo-2-[(4-phenyl-1,3-thiazol-2-yl)amino]acetate Chemical compound C1CCCCC1OC(=O)C(=O)NC(SC=1)=NC=1C1=CC=CC=C1 JBRSGWMGMGXGBZ-UHFFFAOYSA-N 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 1
- 229940075557 diethylene glycol monoethyl ether Drugs 0.000 description 1
- 230000029087 digestion Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 235000019301 disodium ethylene diamine tetraacetate Nutrition 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- JSDDXJXVRWCEBV-UHFFFAOYSA-N ethyl 2-oxo-2-[(4-phenyl-1,3-thiazol-2-yl)amino]acetate Chemical compound S1C(NC(=O)C(=O)OCC)=NC(C=2C=CC=CC=2)=C1 JSDDXJXVRWCEBV-UHFFFAOYSA-N 0.000 description 1
- TUEYHEWXYWCDHA-UHFFFAOYSA-N ethyl 5-methylthiadiazole-4-carboxylate Chemical compound CCOC(=O)C=1N=NSC=1C TUEYHEWXYWCDHA-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 235000020932 food allergy Nutrition 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- IIRDTKBZINWQAW-UHFFFAOYSA-N hexaethylene glycol Chemical compound OCCOCCOCCOCCOCCOCCO IIRDTKBZINWQAW-UHFFFAOYSA-N 0.000 description 1
- FHHGCKHKTAJLOM-UHFFFAOYSA-N hexaethylene glycol monomethyl ether Chemical compound COCCOCCOCCOCCOCCOCCO FHHGCKHKTAJLOM-UHFFFAOYSA-N 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- JBFYUZGYRGXSFL-UHFFFAOYSA-N imidazolide Chemical compound C1=C[N-]C=N1 JBFYUZGYRGXSFL-UHFFFAOYSA-N 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- VVHAVLIDQNWEKF-UHFFFAOYSA-N nonaethylene glycol monomethyl ether Chemical compound COCCOCCOCCOCCOCCOCCOCCOCCOCCO VVHAVLIDQNWEKF-UHFFFAOYSA-N 0.000 description 1
- 239000002687 nonaqueous vehicle Substances 0.000 description 1
- GLZWNFNQMJAZGY-UHFFFAOYSA-N octaethylene glycol Chemical compound OCCOCCOCCOCCOCCOCCOCCOCCO GLZWNFNQMJAZGY-UHFFFAOYSA-N 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- JLFNLZLINWHATN-UHFFFAOYSA-N pentaethylene glycol Chemical compound OCCOCCOCCOCCOCCO JLFNLZLINWHATN-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 229960005323 phenoxyethanol Drugs 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 210000002345 respiratory system Anatomy 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 102200073741 rs121909602 Human genes 0.000 description 1
- 230000008313 sensitization Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 229940083466 soybean lecithin Drugs 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 150000007979 thiazole derivatives Chemical class 0.000 description 1
- 150000003557 thiazoles Chemical class 0.000 description 1
- 231100000816 toxic dose Toxicity 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
- 239000000080 wetting agent Substances 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
- C07D277/38—Nitrogen atoms
- C07D277/44—Acylated amino or imino radicals
- C07D277/46—Acylated amino or imino radicals by carboxylic acids, or sulfur or nitrogen analogues thereof
-
- 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)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Immunology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pulmonology (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19803027527 DE3027527A1 (de) | 1980-07-19 | 1980-07-19 | Neue oxamidsaeure-derivate, verfahren zu ihrer herstellung und diese enthaltende therapeutische mittel |
| DEP3027527.5 | 1980-07-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1180705A true CA1180705A (en) | 1985-01-08 |
Family
ID=6107684
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000381695A Expired CA1180705A (en) | 1980-07-19 | 1981-07-14 | Thiazol-2-yl-oxamic acid derivatives, their preparation and therapeutic agents containing these compounds |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US4407810A (en, 2012) |
| EP (1) | EP0044442B1 (en, 2012) |
| JP (1) | JPS5753475A (en, 2012) |
| AT (1) | ATE6256T1 (en, 2012) |
| CA (1) | CA1180705A (en, 2012) |
| DE (2) | DE3027527A1 (en, 2012) |
| DK (1) | DK149890C (en, 2012) |
| GR (1) | GR75239B (en, 2012) |
| IE (1) | IE51414B1 (en, 2012) |
| ZA (1) | ZA814902B (en, 2012) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1982002384A1 (en) * | 1981-01-08 | 1982-07-22 | Sakano Isao | Their preparation,and medicinal composition containing same |
| IT1183061B (it) * | 1984-07-31 | 1987-10-05 | Zambon Spa | Composti dotati di attivita'antiallergica |
| IT1204960B (it) * | 1987-03-25 | 1989-03-10 | Zambon Farmaceutici Spa | Composti dotati di attivita' antiallergica |
| IT1204959B (it) * | 1987-03-25 | 1989-03-10 | Zambon Farmaceutici Spa | Composti dotati di attivita' antiallergica |
| EP2033688B1 (de) | 2007-08-20 | 2012-10-17 | Symrise AG | Oxalsäurederivate und deren Verwendung als physiologische Kühlwirkstoffe |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH460017A (de) * | 1965-03-05 | 1968-07-31 | Ciba Geigy | Verfahren zur Herstellung neuer Nitrothiazolverbindungen |
| DE2132431A1 (de) * | 1971-06-30 | 1973-01-11 | Riedel De Haen Ag | 4-phenyl-thiazolderivate enthaltende pharmazeutische praeparate |
| AR207563A1 (es) | 1973-03-23 | 1976-10-15 | American Home Prod | Procedimiento para preparar un nuevo ester de acido oxamico |
| US3966965A (en) * | 1973-03-23 | 1976-06-29 | American Home Products Corporation | Oxamic acid derivatives for the prevention of immediate type hypersensitivity reactions |
| DE2601683C3 (de) * | 1976-01-17 | 1982-05-13 | Ytong AG, 8000 München | Kalk-Kieselsäure-Gemisch sowie Verfahren zur Herstellung von dampfgehärteten Baustoffen daraus |
| DE2656468A1 (de) | 1976-12-14 | 1978-06-15 | Boehringer Mannheim Gmbh | N-(benzthiazol-2-yl)-oxamidsaeure- derivate und verfahren zu ihrer herstellung |
| US4150140A (en) | 1976-12-23 | 1979-04-17 | The Upjohn Company | Benzothiazolyl oxanic acids, esters and salts |
| FR2429210A1 (fr) * | 1978-06-19 | 1980-01-18 | Fabre Sa Pierre | Derives de phenyl-4 thiazolyl-2 oxamates utiles dans le traitement de l'asthme |
| DE2828091A1 (de) * | 1978-06-27 | 1980-01-10 | Boehringer Sohn Ingelheim | 4-substituierte thiazoloxamsaeuren sowie ihre salze und ester |
-
1980
- 1980-07-19 DE DE19803027527 patent/DE3027527A1/de not_active Withdrawn
-
1981
- 1981-06-18 GR GR65267A patent/GR75239B/el unknown
- 1981-06-29 AT AT81105025T patent/ATE6256T1/de not_active IP Right Cessation
- 1981-06-29 DE DE8181105025T patent/DE3162277D1/de not_active Expired
- 1981-06-29 EP EP81105025A patent/EP0044442B1/de not_active Expired
- 1981-07-13 US US06/282,661 patent/US4407810A/en not_active Expired - Fee Related
- 1981-07-14 CA CA000381695A patent/CA1180705A/en not_active Expired
- 1981-07-16 IE IE1612/81A patent/IE51414B1/en unknown
- 1981-07-17 ZA ZA814902A patent/ZA814902B/xx unknown
- 1981-07-17 DK DK320081A patent/DK149890C/da active
- 1981-07-17 JP JP56110932A patent/JPS5753475A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| DE3162277D1 (en) | 1984-03-22 |
| EP0044442A1 (de) | 1982-01-27 |
| JPS5753475A (en) | 1982-03-30 |
| DK149890B (da) | 1986-10-20 |
| US4407810A (en) | 1983-10-04 |
| DK320081A (da) | 1982-01-20 |
| DE3027527A1 (de) | 1982-02-18 |
| IE811612L (en) | 1982-01-19 |
| ZA814902B (en) | 1982-08-25 |
| GR75239B (en, 2012) | 1984-07-13 |
| ATE6256T1 (de) | 1984-03-15 |
| EP0044442B1 (de) | 1984-02-15 |
| DK149890C (da) | 1987-04-21 |
| IE51414B1 (en) | 1986-12-24 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0008203B1 (en) | Thiazolidine derivatives, preparing same and pharmaceutical compositions comprising same | |
| CA1190224A (en) | Derivatives of 1,2-diamino-cyclobutene-3,4-dione as potent histamine h.sub.2-antagonists | |
| Aoyama et al. | One pot synthesis using supported reagents system KSCN/SiO2–RNH3OAc/Al2O3: synthesis of 2-aminothiazoles and N-allylthioureas | |
| BRPI0710479A2 (pt) | composto, processo para sua preparaÇço, composiÇço farmacÊutica, uso de um composto e mÉtodo de tratamento de doenÇa ou desosrdem metabàlica. | |
| KR20020058073A (ko) | ｈＰＰＡＲ 알파 활성제로서 치환된 옥사졸 및 티아졸유도체 | |
| WO1986003203A1 (en) | Thienylthiazole derivatives | |
| CA1180705A (en) | Thiazol-2-yl-oxamic acid derivatives, their preparation and therapeutic agents containing these compounds | |
| CA1246071A (en) | 4-substituted thiazole oxamic acids and salts and esters thereof | |
| CA1173838A (en) | Tricyclic thiazolyloxamic acids and their derivatives, their preparation, and therapeutic agents containing these compounds | |
| CA1150272A (en) | 2-(3,4,5-trimethoxyphenyl)-4,5-disubstituted thiazoles | |
| EP0099121A2 (en) | Pharmaceutical compositions | |
| KR100859591B1 (ko) | Ｈｐｐａｒ-알파 수용체의 옥사졸/티아졸-유도체 활성제 | |
| US2255903A (en) | 5,5-disubstituted-2,4-thiazolidiones, and process of making them | |
| CA1180706A (en) | Cycloalkano-thiazolyloxamic acid derivatives, their preparation and therapeutic agents containing these compounds | |
| US3523122A (en) | Novel 5-nitro-4-thiazolin-2-ylidene compounds | |
| US4348403A (en) | 2-Amino-4-(4-benzyloxyphenyl)thiazoles, and their use in hyperlipemia | |
| BRPI0610832A2 (pt) | tiazolidinonas sem nitrogênio básico, sua produção e uso como agentes farmacêuticos | |
| US2780628A (en) | 2-substituted aromatic thiazoles | |
| SE448732B (sv) | N-(5-tetrazolyl)-1-oxo-1h-tiazolo /3,2-a/-pyrimidin-2-karboxamider med antiallergisk och antiulceros verkan samt motsvarande 2-karboxylsyror | |
| JPS5925381A (ja) | 新規なフエニル酢酸誘導体 | |
| JP3190959B2 (ja) | ４−メチル−５−（２−クロロエチル）−チアゾールおよびその同族体の新規な製法 | |
| CA2075998A1 (en) | 4-methyl thiazole derivatives, preparation methods therefor and pharmaceutical compositions containing said derivatives | |
| JPS56104876A (en) | Thiazolidine derivative | |
| KR800000040B1 (ko) | 4-하이드록시-2H-나프토[2,1-e]-1,2-티아진-3-카복사마이드-1,1-디옥사이드류의 제조방법 | |
| DD153838A5 (de) | Verfahren zur herstellung von 3,4-disubstituierten 1,2,5-thiadiazol-1-oxiden und-1,1-dioxiden |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |