CN1100425A - 噻唑并嘧啶衍生物 - Google Patents

噻唑并嘧啶衍生物 Download PDF

Info

Publication number: CN1100425A
Authority: CN; China
Prior art keywords: carbon atoms; group; pyrimidine; thiazolo; dihydro
Prior art date: 1993-04-01
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.): Pending

Application number

CN94105279A

Other languages

English (en)

Chinese (zh)

Inventor

松本裕生

田中纪子

中山清

茶谷晴子

岩花伦生

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

Daiichi Pharmaceutical Co Ltd

Original Assignee

Daiichi Pharmaceutical Co Ltd

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1993-04-01

Filing date

1994-04-01

Publication date

1995-03-22

1994-04-01 Application filed by Daiichi Pharmaceutical Co Ltd filed Critical Daiichi Pharmaceutical Co Ltd

1995-03-22 Publication of CN1100425A publication Critical patent/CN1100425A/zh

Status Pending legal-status Critical Current

Links

150000008634 thiazolopyrimidines Chemical class 0.000 title claims abstract description 5
150000003839 salts Chemical class 0.000 claims abstract description 20
230000001772 anti-angiogenic effect Effects 0.000 claims abstract description 12
125000001424 substituent group Chemical group 0.000 claims abstract description 11
150000001875 compounds Chemical class 0.000 claims description 123
125000004432 carbon atom Chemical group C* 0.000 claims description 72
239000000203 mixture Substances 0.000 claims description 67
-1 nitro, sulfo Chemical group 0.000 claims description 49
125000000217 alkyl group Chemical group 0.000 claims description 35
229920006395 saturated elastomer Polymers 0.000 claims description 35
125000003118 aryl group Chemical group 0.000 claims description 30
125000003545 alkoxy group Chemical group 0.000 claims description 19
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
125000004181 carboxyalkyl group Chemical group 0.000 claims description 11
125000002887 hydroxy group Chemical group [H]O* 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 9
125000003342 alkenyl group Chemical group 0.000 claims description 8
125000000753 cycloalkyl group Chemical group 0.000 claims description 8
125000005843 halogen group Chemical group 0.000 claims description 8
125000004430 oxygen atom Chemical group O* 0.000 claims description 8
125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 7
125000000623 heterocyclic group Chemical group 0.000 claims description 7
238000002360 preparation method Methods 0.000 claims description 6
125000004966 cyanoalkyl group Chemical group 0.000 claims description 5
125000000000 cycloalkoxy group Chemical group 0.000 claims description 5
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 5
229910052717 sulfur Inorganic materials 0.000 claims description 5
125000005819 alkenylalkoxy group Chemical group 0.000 claims description 4
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 4
125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 4
125000005085 alkoxycarbonylalkoxy group Chemical group 0.000 claims description 4
125000005111 carboxyalkoxy group Chemical group 0.000 claims description 4
125000001188 haloalkyl group Chemical group 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
238000006467 substitution reaction Methods 0.000 claims description 4
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 4
125000004434 sulfur atom Chemical group 0.000 claims description 4
125000005330 8 membered heterocyclic group Chemical group 0.000 claims description 3
229940077388 benzenesulfonate Drugs 0.000 claims description 3
239000003937 drug carrier Substances 0.000 claims 1
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims 1
230000033115 angiogenesis Effects 0.000 abstract description 7
206010012689 Diabetic retinopathy Diseases 0.000 abstract description 4
206010027476 Metastases Diseases 0.000 abstract description 4
201000004681 Psoriasis Diseases 0.000 abstract description 4
230000012010 growth Effects 0.000 abstract description 4
230000009401 metastasis Effects 0.000 abstract description 4
201000010099 disease Diseases 0.000 abstract description 3
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 3
201000011510 cancer Diseases 0.000 abstract description 2
208000037976 chronic inflammation Diseases 0.000 abstract description 2
230000006020 chronic inflammation Effects 0.000 abstract description 2
238000011161 development Methods 0.000 abstract description 2
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 143
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 142
238000002844 melting Methods 0.000 description 121
230000008018 melting Effects 0.000 description 121
238000000921 elemental analysis Methods 0.000 description 112
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 109
229910000041 hydrogen chloride Inorganic materials 0.000 description 109
239000000243 solution Substances 0.000 description 78
238000005160 1H NMR spectroscopy Methods 0.000 description 73
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 72
239000002904 solvent Substances 0.000 description 67
239000013078 crystal Substances 0.000 description 50
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 46
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 45
238000003756 stirring Methods 0.000 description 42
239000011541 reaction mixture Substances 0.000 description 41
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 40
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 38
238000001914 filtration Methods 0.000 description 38
238000006243 chemical reaction Methods 0.000 description 36
238000001816 cooling Methods 0.000 description 31
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 30
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 28
238000010992 reflux Methods 0.000 description 25
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 24
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 23
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 22
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
239000002253 acid Substances 0.000 description 20
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 20
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 18
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 17
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 16
239000000460 chlorine Substances 0.000 description 15
239000012046 mixed solvent Substances 0.000 description 15
229910000030 sodium bicarbonate Inorganic materials 0.000 description 15
235000017557 sodium bicarbonate Nutrition 0.000 description 15
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
239000000725 suspension Substances 0.000 description 14
238000000034 method Methods 0.000 description 13
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
239000012141 concentrate Substances 0.000 description 12
235000008504 concentrate Nutrition 0.000 description 12
239000012044 organic layer Substances 0.000 description 12
239000011780 sodium chloride Substances 0.000 description 12
229910052799 carbon Inorganic materials 0.000 description 11
238000010438 heat treatment Methods 0.000 description 11
239000000741 silica gel Substances 0.000 description 11
229910002027 silica gel Inorganic materials 0.000 description 11
238000010898 silica gel chromatography Methods 0.000 description 11
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 10
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
150000001721 carbon Chemical group 0.000 description 10
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
239000007864 aqueous solution Substances 0.000 description 9
238000009833 condensation Methods 0.000 description 9
230000005494 condensation Effects 0.000 description 9
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 9
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 8
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 8
239000000843 powder Substances 0.000 description 8
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 8
NVHNGVXBCWYLFA-UHFFFAOYSA-N 1,3-diazinane-2-thione Chemical compound S=C1NCCCN1 NVHNGVXBCWYLFA-UHFFFAOYSA-N 0.000 description 7
YCXCVZPIEQPHHB-UHFFFAOYSA-N 3-n,5-n-dimethylpyridine-3,5-diamine Chemical compound CNC1=CN=CC(NC)=C1 YCXCVZPIEQPHHB-UHFFFAOYSA-N 0.000 description 7
238000004440 column chromatography Methods 0.000 description 7
229910000027 potassium carbonate Inorganic materials 0.000 description 7
238000007363 ring formation reaction Methods 0.000 description 7
UQRLKWGPEVNVHT-UHFFFAOYSA-N 3,5-dichloroaniline Chemical compound NC1=CC(Cl)=CC(Cl)=C1 UQRLKWGPEVNVHT-UHFFFAOYSA-N 0.000 description 6
239000003795 chemical substances by application Substances 0.000 description 6
230000000694 effects Effects 0.000 description 6
239000003480 eluent Substances 0.000 description 6
150000007529 inorganic bases Chemical class 0.000 description 6
239000000126 substance Substances 0.000 description 6
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 5
230000002378 acidificating effect Effects 0.000 description 5
150000001412 amines Chemical class 0.000 description 5
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
238000000354 decomposition reaction Methods 0.000 description 5
238000000605 extraction Methods 0.000 description 5
PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
MKARNSWMMBGSHX-UHFFFAOYSA-N 3,5-dimethylaniline Chemical compound CC1=CC(C)=CC(N)=C1 MKARNSWMMBGSHX-UHFFFAOYSA-N 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 4
150000001298 alcohols Chemical class 0.000 description 4
125000004453 alkoxycarbonyl group Chemical group 0.000 description 4
150000001805 chlorine compounds Chemical class 0.000 description 4
210000003711 chorioallantoic membrane Anatomy 0.000 description 4
238000002425 crystallisation Methods 0.000 description 4
230000008025 crystallization Effects 0.000 description 4
FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 4
LBAQSKZHMLAFHH-UHFFFAOYSA-N ethoxyethane;hydron;chloride Chemical class Cl.CCOCC LBAQSKZHMLAFHH-UHFFFAOYSA-N 0.000 description 4
MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 4
FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
150000004820 halides Chemical class 0.000 description 4
238000006460 hydrolysis reaction Methods 0.000 description 4
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
238000001953 recrystallisation Methods 0.000 description 4
238000012360 testing method Methods 0.000 description 4
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 3
JMXLHQFPEWUAGX-UHFFFAOYSA-N 4-heptylsulfanylaniline Chemical compound CCCCCCCSC1=CC=C(N)C=C1 JMXLHQFPEWUAGX-UHFFFAOYSA-N 0.000 description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000000654 additive Substances 0.000 description 3
239000002671 adjuvant Substances 0.000 description 3
150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
229910052794 bromium Inorganic materials 0.000 description 3
150000001735 carboxylic acids Chemical class 0.000 description 3
238000005660 chlorination reaction Methods 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 3
235000013601 eggs Nutrition 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
150000002170 ethers Chemical class 0.000 description 3
230000002140 halogenating effect Effects 0.000 description 3
230000007062 hydrolysis Effects 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
238000000746 purification Methods 0.000 description 3
FUXJMHXHGDAHPD-UHFFFAOYSA-N pyrimidine-2-carboxamide Chemical compound NC(=O)C1=NC=CC=N1 FUXJMHXHGDAHPD-UHFFFAOYSA-N 0.000 description 3
HBCQSNAFLVXVAY-UHFFFAOYSA-N pyrimidine-2-thiol Chemical compound SC1=NC=CC=N1 HBCQSNAFLVXVAY-UHFFFAOYSA-N 0.000 description 3
239000007787 solid Substances 0.000 description 3
238000005406 washing Methods 0.000 description 3
239000008096 xylene Substances 0.000 description 3
HHNWXGDPIZHNBP-UHFFFAOYSA-N 3,6,6-trimethyl-5,7-dihydro-[1,3]thiazolo[3,2-a]pyrimidine-2-carboxylic acid;hydrochloride Chemical compound Cl.C1C(C)(C)CN2C(C)=C(C(O)=O)SC2=N1 HHNWXGDPIZHNBP-UHFFFAOYSA-N 0.000 description 2
CUYKNJBYIJFRCU-UHFFFAOYSA-N 3-aminopyridine Chemical compound NC1=CC=CN=C1 CUYKNJBYIJFRCU-UHFFFAOYSA-N 0.000 description 2
HGINADPHJQTSKN-UHFFFAOYSA-M 3-ethoxy-3-oxopropanoate Chemical compound CCOC(=O)CC([O-])=O HGINADPHJQTSKN-UHFFFAOYSA-M 0.000 description 2
OMKLUFVSNUSRIH-UHFFFAOYSA-N 3-methyl-6,7-dihydro-5h-[1,3]thiazolo[3,2-a]pyrimidine-2-carboxylic acid;hydrochloride Chemical compound Cl.C1CCN2C(C)=C(C(O)=O)SC2=N1 OMKLUFVSNUSRIH-UHFFFAOYSA-N 0.000 description 2
FAXATELCDLPMFF-UHFFFAOYSA-N 3-pentyl-6,7-dihydro-5h-[1,3]thiazolo[3,2-a]pyrimidine-2-carboxylic acid;hydrochloride Chemical compound Cl.C1CCN2C(CCCCC)=C(C(O)=O)SC2=N1 FAXATELCDLPMFF-UHFFFAOYSA-N 0.000 description 2
QRXIVPJRURKDRC-UHFFFAOYSA-N 3-propan-2-yl-6,7-dihydro-5h-[1,3]thiazolo[3,2-a]pyrimidine-2-carboxylic acid;hydrochloride Chemical compound Cl.C1CCN2C(C(C)C)=C(C(O)=O)SC2=N1 QRXIVPJRURKDRC-UHFFFAOYSA-N 0.000 description 2
QFIQIWMTHPOLQN-UHFFFAOYSA-N 3-propyl-6,7-dihydro-5h-[1,3]thiazolo[3,2-a]pyrimidine-2-carboxylic acid;hydrochloride Chemical compound Cl.C1CCN2C(CCC)=C(C(O)=O)SC2=N1 QFIQIWMTHPOLQN-UHFFFAOYSA-N 0.000 description 2
QQJRVHNBPZOLGW-UHFFFAOYSA-N 4-heptylsulfonylaniline Chemical compound CCCCCCCS(=O)(=O)C1=CC=C(N)C=C1 QQJRVHNBPZOLGW-UHFFFAOYSA-N 0.000 description 2
CYJRNFFLTBEQSQ-UHFFFAOYSA-N 8-(3-methyl-1-benzothiophen-5-yl)-N-(4-methylsulfonylpyridin-3-yl)quinoxalin-6-amine Chemical compound CS(=O)(=O)C1=C(C=NC=C1)NC=1C=C2N=CC=NC2=C(C=1)C=1C=CC2=C(C(=CS2)C)C=1 CYJRNFFLTBEQSQ-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
206010061218 Inflammation Diseases 0.000 description 2
AYCPARAPKDAOEN-LJQANCHMSA-N N-[(1S)-2-(dimethylamino)-1-phenylethyl]-6,6-dimethyl-3-[(2-methyl-4-thieno[3,2-d]pyrimidinyl)amino]-1,4-dihydropyrrolo[3,4-c]pyrazole-5-carboxamide Chemical compound C1([C@H](NC(=O)N2C(C=3NN=C(NC=4C=5SC=CC=5N=C(C)N=4)C=3C2)(C)C)CN(C)C)=CC=CC=C1 AYCPARAPKDAOEN-LJQANCHMSA-N 0.000 description 2
JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 2
206010028980 Neoplasm Diseases 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
238000003556 assay Methods 0.000 description 2
IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
239000004305 biphenyl Substances 0.000 description 2
235000010290 biphenyl Nutrition 0.000 description 2
238000009835 boiling Methods 0.000 description 2
150000001649 bromium compounds Chemical class 0.000 description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
239000012320 chlorinating reagent Substances 0.000 description 2
125000004093 cyano group Chemical group *C#N 0.000 description 2
238000004090 dissolution Methods 0.000 description 2
238000001035 drying Methods 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
DZGCGKFAPXFTNM-UHFFFAOYSA-N ethanol;hydron;chloride Chemical class Cl.CCO DZGCGKFAPXFTNM-UHFFFAOYSA-N 0.000 description 2
FOIBGHJHUMDYGZ-UHFFFAOYSA-N ethyl 2-[[2-[(3,5-dichlorophenyl)carbamoyl]-6,7-dihydro-5h-[1,3]thiazolo[3,2-a]pyrimidin-3-yl]oxy]acetate Chemical compound S1C2=NCCCN2C(OCC(=O)OCC)=C1C(=O)NC1=CC(Cl)=CC(Cl)=C1 FOIBGHJHUMDYGZ-UHFFFAOYSA-N 0.000 description 2
QTUCSQBKVJZYSS-UHFFFAOYSA-N ethyl 3-(3,5-dichloroanilino)propanoate Chemical compound CCOC(=O)CCNC1=CC(Cl)=CC(Cl)=C1 QTUCSQBKVJZYSS-UHFFFAOYSA-N 0.000 description 2
GPIWDGKEXCGUOU-UHFFFAOYSA-N ethyl 3-[2-[(4-octylphenyl)carbamoyl]-6,7-dihydro-5h-[1,3]thiazolo[3,2-a]pyrimidin-3-yl]propanoate;hydrochloride Chemical compound Cl.C1=CC(CCCCCCCC)=CC=C1NC(=O)C(S1)=C(CCC(=O)OCC)N2C1=NCCC2 GPIWDGKEXCGUOU-UHFFFAOYSA-N 0.000 description 2
DVRQYARNOYDEKA-UHFFFAOYSA-N ethyl 6-[4-[(3-propyl-6,7-dihydro-5h-[1,3]thiazolo[3,2-a]pyrimidine-2-carbonyl)amino]phenyl]sulfanylhexanoate;hydrochloride Chemical class Cl.S1C2=NCCCN2C(CCC)=C1C(=O)NC1=CC=C(SCCCCCC(=O)OCC)C=C1 DVRQYARNOYDEKA-UHFFFAOYSA-N 0.000 description 2
150000002222 fluorine compounds Chemical class 0.000 description 2
238000009472 formulation Methods 0.000 description 2
NGGMYCMLYOUNGM-CSDLUJIJSA-N fumagillin Chemical compound C([C@H]([C@H]([C@@H]1[C@]2(C)[C@H](O2)CC=C(C)C)OC)OC(=O)\C=C\C=C\C=C\C=C\C(O)=O)C[C@@]21CO2 NGGMYCMLYOUNGM-CSDLUJIJSA-N 0.000 description 2
230000004054 inflammatory process Effects 0.000 description 2
230000002401 inhibitory effect Effects 0.000 description 2
230000005764 inhibitory process Effects 0.000 description 2
150000004694 iodide salts Chemical class 0.000 description 2
VXTVRZIUOJSIIN-UHFFFAOYSA-N methyl 4-(3-aminophenyl)benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=CC=CC(N)=C1 VXTVRZIUOJSIIN-UHFFFAOYSA-N 0.000 description 2
PMHCOLXQSXMKJJ-UHFFFAOYSA-N methyl 4-(3-nitrophenyl)benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=CC=CC([N+]([O-])=O)=C1 PMHCOLXQSXMKJJ-UHFFFAOYSA-N 0.000 description 2
RVQMBBZSVAFGST-UHFFFAOYSA-N n-(3,5-dichlorophenyl)-3-hydroxy-6,7-dihydro-5h-[1,3]thiazolo[3,2-a]pyrimidine-2-carboxamide Chemical compound S1C2=NCCCN2C(O)=C1C(=O)NC1=CC(Cl)=CC(Cl)=C1 RVQMBBZSVAFGST-UHFFFAOYSA-N 0.000 description 2
KWUGDHDWKFNWRR-UHFFFAOYSA-N n-(4-methoxyphenyl)-3-propyl-6,7-dihydro-5h-[1,3]thiazolo[3,2-a]pyrimidine-2-carboxamide;hydrochloride Chemical compound Cl.S1C2=NCCCN2C(CCC)=C1C(=O)NC1=CC=C(OC)C=C1 KWUGDHDWKFNWRR-UHFFFAOYSA-N 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 2
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
238000001556 precipitation Methods 0.000 description 2
YKSDLYFRZAUBMW-UHFFFAOYSA-N pyrimidine-2-carboxamide;hydrochloride Chemical compound Cl.NC(=O)C1=NC=CC=N1 YKSDLYFRZAUBMW-UHFFFAOYSA-N 0.000 description 2
238000011160 research Methods 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
239000007858 starting material Substances 0.000 description 2
FPQNBUFJNDTMPS-UHFFFAOYSA-N tert-butyl 3-cyclobutyl-3-oxopropanoate Chemical compound CC(C)(C)OC(=O)CC(=O)C1CCC1 FPQNBUFJNDTMPS-UHFFFAOYSA-N 0.000 description 2
XHJXQLDHCLJJLW-UHFFFAOYSA-N tert-butyl 3-methyl-6,7-dihydro-5h-[1,3]thiazolo[3,2-a]pyrimidine-2-carboxylate;hydrochloride Chemical compound Cl.C1CCN2C(C)=C(C(=O)OC(C)(C)C)SC2=N1 XHJXQLDHCLJJLW-UHFFFAOYSA-N 0.000 description 2
JKUYRAMKJLMYLO-UHFFFAOYSA-N tert-butyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OC(C)(C)C JKUYRAMKJLMYLO-UHFFFAOYSA-N 0.000 description 2
IQCFKDXFNXQEKV-UHFFFAOYSA-N tert-butyl 3-oxononanoate Chemical compound CCCCCCC(=O)CC(=O)OC(C)(C)C IQCFKDXFNXQEKV-UHFFFAOYSA-N 0.000 description 2
BTHNEHUFXUBOQG-UHFFFAOYSA-N tert-butyl 4-methyl-3-oxopentanoate Chemical compound CC(C)C(=O)CC(=O)OC(C)(C)C BTHNEHUFXUBOQG-UHFFFAOYSA-N 0.000 description 2
NGGMYCMLYOUNGM-UHFFFAOYSA-N (-)-fumagillin Natural products O1C(CC=C(C)C)C1(C)C1C(OC)C(OC(=O)C=CC=CC=CC=CC(O)=O)CCC21CO2 NGGMYCMLYOUNGM-UHFFFAOYSA-N 0.000 description 1
VCGRFBXVSFAGGA-UHFFFAOYSA-N (1,1-dioxo-1,4-thiazinan-4-yl)-[6-[[3-(4-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]methoxy]pyridin-3-yl]methanone Chemical compound CC=1ON=C(C=2C=CC(F)=CC=2)C=1COC(N=C1)=CC=C1C(=O)N1CCS(=O)(=O)CC1 VCGRFBXVSFAGGA-UHFFFAOYSA-N 0.000 description 1
BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
QGLWBTPVKHMVHM-KTKRTIGZSA-N (z)-octadec-9-en-1-amine Chemical compound CCCCCCCC\C=C/CCCCCCCCN QGLWBTPVKHMVHM-KTKRTIGZSA-N 0.000 description 1
WORJRXHJTUTINR-UHFFFAOYSA-N 1,4-dioxane;hydron;chloride Chemical class Cl.C1COCCO1 WORJRXHJTUTINR-UHFFFAOYSA-N 0.000 description 1
CZQLPPUSDAIQMD-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)-3-spiro[5,6,7,8-tetrahydro-3,1-benzothiazine-4,1'-cyclohexane]-2-ylurea Chemical compound C1=C(Cl)C(Cl)=CC=C1NC(=O)NC(SC12CCCCC2)=NC2=C1CCCC2 CZQLPPUSDAIQMD-UHFFFAOYSA-N 0.000 description 1
LSXKDWGTSHCFPP-UHFFFAOYSA-N 1-bromoheptane Chemical compound CCCCCCCBr LSXKDWGTSHCFPP-UHFFFAOYSA-N 0.000 description 1
125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
XOKACGLLWOYHDI-UHFFFAOYSA-N 1-o-tert-butyl 6-o-ethyl 3-oxohexanedioate Chemical compound CCOC(=O)CCC(=O)CC(=O)OC(C)(C)C XOKACGLLWOYHDI-UHFFFAOYSA-N 0.000 description 1
VTMDZQAVHKPMOJ-UHFFFAOYSA-N 2,5-dichloro-4-[(3-propyl-6,7-dihydro-5h-[1,3]thiazolo[3,2-a]pyrimidine-2-carbonyl)amino]benzenesulfonic acid;hydrochloride Chemical compound Cl.S1C2=NCCCN2C(CCC)=C1C(=O)NC1=CC(Cl)=C(S(O)(=O)=O)C=C1Cl VTMDZQAVHKPMOJ-UHFFFAOYSA-N 0.000 description 1
NAZDVUBIEPVUKE-UHFFFAOYSA-N 2,5-dimethoxyaniline Chemical compound COC1=CC=C(OC)C(N)=C1 NAZDVUBIEPVUKE-UHFFFAOYSA-N 0.000 description 1
GHIQOSBELDYSMP-UHFFFAOYSA-N 2-[[2-[(3,5-dichlorophenyl)carbamoyl]-6,7-dihydro-5h-[1,3]thiazolo[3,2-a]pyrimidin-3-yl]oxy]acetic acid Chemical compound S1C2=NCCCN2C(OCC(=O)O)=C1C(=O)NC1=CC(Cl)=CC(Cl)=C1 GHIQOSBELDYSMP-UHFFFAOYSA-N 0.000 description 1
125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
JTUADIPAALOMFL-UHFFFAOYSA-N 3,5-dichloro-n-methylaniline Chemical compound CNC1=CC(Cl)=CC(Cl)=C1 JTUADIPAALOMFL-UHFFFAOYSA-N 0.000 description 1
BCPDLXLVSAQENP-UHFFFAOYSA-N 3,6,6-trimethyl-n-octyl-5,7-dihydro-[1,3]thiazolo[3,2-a]pyrimidine-2-carboxamide;hydrochloride Chemical compound Cl.C1C(C)(C)CN=C2SC(C(=O)NCCCCCCCC)=C(C)N21 BCPDLXLVSAQENP-UHFFFAOYSA-N 0.000 description 1
UOGHYGYYCAORQZ-UHFFFAOYSA-N 3-(2-cyanoethyl)-n-(4-octylphenyl)-6,7-dihydro-5h-[1,3]thiazolo[3,2-a]pyrimidine-2-carboxamide;hydrochloride Chemical compound Cl.C1=CC(CCCCCCCC)=CC=C1NC(=O)C(S1)=C(CCC#N)N2C1=NCCC2 UOGHYGYYCAORQZ-UHFFFAOYSA-N 0.000 description 1
PWGHRMSFUVLBMB-UHFFFAOYSA-N 3-(3,5-dichloro-n-(3-propyl-6,7-dihydro-5h-[1,3]thiazolo[3,2-a]pyrimidine-2-carbonyl)anilino)propanoic acid;hydrochloride Chemical compound Cl.S1C2=NCCCN2C(CCC)=C1C(=O)N(CCC(O)=O)C1=CC(Cl)=CC(Cl)=C1 PWGHRMSFUVLBMB-UHFFFAOYSA-N 0.000 description 1
RQZYPPHRJSCLJW-UHFFFAOYSA-N 3-(3-cyanopropyl)-n-(4-octylphenyl)-6,7-dihydro-5h-[1,3]thiazolo[3,2-a]pyrimidine-2-carboxamide;hydrochloride Chemical compound Cl.C1=CC(CCCCCCCC)=CC=C1NC(=O)C(S1)=C(CCCC#N)N2C1=NCCC2 RQZYPPHRJSCLJW-UHFFFAOYSA-N 0.000 description 1
VCGRTDZPYFZCCB-UHFFFAOYSA-N 3-(3-ethoxy-3-oxopropyl)-6,7-dihydro-5h-[1,3]thiazolo[3,2-a]pyrimidine-2-carboxylic acid;hydrochloride Chemical compound Cl.C1CCN2C(CCC(=O)OCC)=C(C(O)=O)SC2=N1 VCGRTDZPYFZCCB-UHFFFAOYSA-N 0.000 description 1
DCNZRWBUSRSIRS-UHFFFAOYSA-N 3-[2-[(4-octylphenyl)carbamoyl]-6,7-dihydro-5h-[1,3]thiazolo[3,2-a]pyrimidin-3-yl]propanoic acid;hydrochloride Chemical compound Cl.C1=CC(CCCCCCCC)=CC=C1NC(=O)C(S1)=C(CCC(O)=O)N2C1=NCCC2 DCNZRWBUSRSIRS-UHFFFAOYSA-N 0.000 description 1
XGLSACKVIBAPDF-UHFFFAOYSA-N 3-[4-[[3-(ethoxymethyl)-6,7-dihydro-5h-[1,3]thiazolo[3,2-a]pyrimidine-2-carbonyl]amino]phenyl]sulfanylpropanoic acid;hydrochloride Chemical class Cl.S1C2=NCCCN2C(COCC)=C1C(=O)NC1=CC=C(SCCC(O)=O)C=C1 XGLSACKVIBAPDF-UHFFFAOYSA-N 0.000 description 1
125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
ARPOJLNYWSQTCH-UHFFFAOYSA-N 3-butyl-n-(3,5-dichlorophenyl)-6,7-dihydro-5h-[1,3]thiazolo[3,2-a]pyrimidine-2-carboxamide;hydrochloride Chemical compound Cl.S1C2=NCCCN2C(CCCC)=C1C(=O)NC1=CC(Cl)=CC(Cl)=C1 ARPOJLNYWSQTCH-UHFFFAOYSA-N 0.000 description 1
PVYJKQPTHQHCQJ-UHFFFAOYSA-N 3-butyl-n-(3,5-dichlorophenyl)-n-methyl-6,7-dihydro-5h-[1,3]thiazolo[3,2-a]pyrimidine-2-carboxamide;hydrochloride Chemical compound Cl.S1C2=NCCCN2C(CCCC)=C1C(=O)N(C)C1=CC(Cl)=CC(Cl)=C1 PVYJKQPTHQHCQJ-UHFFFAOYSA-N 0.000 description 1
OZOBBPSCWYDDAX-UHFFFAOYSA-N 3-butyl-n-(3,5-difluorophenyl)-6,7-dihydro-5h-[1,3]thiazolo[3,2-a]pyrimidine-2-carboxamide;hydrochloride Chemical compound Cl.S1C2=NCCCN2C(CCCC)=C1C(=O)NC1=CC(F)=CC(F)=C1 OZOBBPSCWYDDAX-UHFFFAOYSA-N 0.000 description 1
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
JKPXIUVKPRYVAF-UHFFFAOYSA-N 3-cyclobutyl-6,7-dihydro-5h-[1,3]thiazolo[3,2-a]pyrimidine-2-carbonyl chloride Chemical compound N12CCCN=C2SC(C(=O)Cl)=C1C1CCC1 JKPXIUVKPRYVAF-UHFFFAOYSA-N 0.000 description 1
IPSCWLFWHNNNLE-UHFFFAOYSA-N 3-cyclobutyl-6,7-dihydro-5h-[1,3]thiazolo[3,2-a]pyrimidine-2-carboxamide;hydrochloride Chemical compound Cl.N12CCCN=C2SC(C(=O)N)=C1C1CCC1 IPSCWLFWHNNNLE-UHFFFAOYSA-N 0.000 description 1
VHMSUVLSGQKOTP-UHFFFAOYSA-N 3-cyclobutyl-6,7-dihydro-5h-[1,3]thiazolo[3,2-a]pyrimidine-2-carboxylic acid Chemical compound N12CCCN=C2SC(C(=O)O)=C1C1CCC1 VHMSUVLSGQKOTP-UHFFFAOYSA-N 0.000 description 1
WJTPRUAYEWVMNA-UHFFFAOYSA-N 3-cyclobutyl-6,7-dihydro-5h-[1,3]thiazolo[3,2-a]pyrimidine-2-carboxylic acid;hydrochloride Chemical compound Cl.N12CCCN=C2SC(C(=O)O)=C1C1CCC1 WJTPRUAYEWVMNA-UHFFFAOYSA-N 0.000 description 1
VUQRQEAMECZVAA-UHFFFAOYSA-N 3-cyclobutyl-n-(3,5-dichlorophenyl)-6,7-dihydro-5h-[1,3]thiazolo[3,2-a]pyrimidine-2-carboxamide;hydrochloride Chemical compound Cl.ClC1=CC(Cl)=CC(NC(=O)C=2SC3=NCCCN3C=2C2CCC2)=C1 VUQRQEAMECZVAA-UHFFFAOYSA-N 0.000 description 1
YSNHRCICLKODED-UHFFFAOYSA-N 3-cyclobutyl-n-(4-decylphenyl)-6,7-dihydro-5h-[1,3]thiazolo[3,2-a]pyrimidine-2-carboxamide;hydrochloride Chemical compound Cl.C1=CC(CCCCCCCCCC)=CC=C1NC(=O)C(SC1=NCCCN11)=C1C1CCC1 YSNHRCICLKODED-UHFFFAOYSA-N 0.000 description 1
UPNPCWHUIGVWMA-UHFFFAOYSA-N 3-cyclobutyl-n-(4-octylphenyl)-6,7-dihydro-5h-[1,3]thiazolo[3,2-a]pyrimidine-2-carboxamide;hydrochloride Chemical compound Cl.C1=CC(CCCCCCCC)=CC=C1NC(=O)C(SC1=NCCCN11)=C1C1CCC1 UPNPCWHUIGVWMA-UHFFFAOYSA-N 0.000 description 1
DROYTZNCGATHMG-UHFFFAOYSA-N 3-cyclohexyl-n-(3,5-dichlorophenyl)-6,7-dihydro-5h-[1,3]thiazolo[3,2-a]pyrimidine-2-carboxamide;hydrochloride Chemical compound Cl.ClC1=CC(Cl)=CC(NC(=O)C=2SC3=NCCCN3C=2C2CCCCC2)=C1 DROYTZNCGATHMG-UHFFFAOYSA-N 0.000 description 1
BXLBGDBSOZTFEE-UHFFFAOYSA-N 3-cyclohexyl-n-(3,5-dichlorophenyl)-n-methyl-6,7-dihydro-5h-[1,3]thiazolo[3,2-a]pyrimidine-2-carboxamide;hydrochloride Chemical compound Cl.C=1C(Cl)=CC(Cl)=CC=1N(C)C(=O)C(SC1=NCCCN11)=C1C1CCCCC1 BXLBGDBSOZTFEE-UHFFFAOYSA-N 0.000 description 1
ZQYMPXRTZDDMJM-UHFFFAOYSA-N 3-cyclopentyl-n-(3,5-dichlorophenyl)-6,7-dihydro-5h-[1,3]thiazolo[3,2-a]pyrimidine-2-carboxamide;hydrochloride Chemical compound Cl.ClC1=CC(Cl)=CC(NC(=O)C=2SC3=NCCCN3C=2C2CCCC2)=C1 ZQYMPXRTZDDMJM-UHFFFAOYSA-N 0.000 description 1
QXCKGMHZOGIMLX-UHFFFAOYSA-N 3-cyclopropyl-n-(3,5-dichlorophenyl)-6,7-dihydro-5h-[1,3]thiazolo[3,2-a]pyrimidine-2-carboxamide;hydrochloride Chemical compound Cl.ClC1=CC(Cl)=CC(NC(=O)C=2SC3=NCCCN3C=2C2CC2)=C1 QXCKGMHZOGIMLX-UHFFFAOYSA-N 0.000 description 1
SMZHGVWNQCRYKK-UHFFFAOYSA-N 3-cyclopropyl-n-(3,5-dichlorophenyl)-n-methyl-6,7-dihydro-5h-[1,3]thiazolo[3,2-a]pyrimidine-2-carboxamide;hydrochloride Chemical class Cl.C=1C(Cl)=CC(Cl)=CC=1N(C)C(=O)C(SC1=NCCCN11)=C1C1CC1 SMZHGVWNQCRYKK-UHFFFAOYSA-N 0.000 description 1
ORFWUIHVWZLPSG-UHFFFAOYSA-N 3-cyclopropyl-n-(3,5-dimethoxyphenyl)-6,7-dihydro-5h-[1,3]thiazolo[3,2-a]pyrimidine-2-carboxamide;hydrochloride Chemical compound Cl.COC1=CC(OC)=CC(NC(=O)C=2SC3=NCCCN3C=2C2CC2)=C1 ORFWUIHVWZLPSG-UHFFFAOYSA-N 0.000 description 1
KRIBCZQJTCSIMI-UHFFFAOYSA-N 3-cyclopropyl-n-(4-octylphenyl)-6,7-dihydro-5h-[1,3]thiazolo[3,2-a]pyrimidine-2-carboxamide;hydrochloride Chemical compound Cl.C1=CC(CCCCCCCC)=CC=C1NC(=O)C(SC1=NCCCN11)=C1C1CC1 KRIBCZQJTCSIMI-UHFFFAOYSA-N 0.000 description 1
AOPRWGPFBNYHCL-UHFFFAOYSA-N 3-ethyl-n-(4-heptylphenyl)-6,7-dihydro-5h-[1,3]thiazolo[3,2-a]pyrimidine-2-carboxamide;hydrochloride Chemical compound Cl.C1=CC(CCCCCCC)=CC=C1NC(=O)C(S1)=C(CC)N2C1=NCCC2 AOPRWGPFBNYHCL-UHFFFAOYSA-N 0.000 description 1
JOCREXQLEMWINJ-UHFFFAOYSA-N 3-ethyl-n-(4-octylphenyl)-6,7-dihydro-5h-[1,3]thiazolo[3,2-a]pyrimidine-2-carboxamide;hydrochloride Chemical compound Cl.C1=CC(CCCCCCCC)=CC=C1NC(=O)C(S1)=C(CC)N2C1=NCCC2 JOCREXQLEMWINJ-UHFFFAOYSA-N 0.000 description 1
VXORTRSCEMECGR-UHFFFAOYSA-N 3-hydroxy-n-(2-octylphenyl)-6,7-dihydro-5h-[1,3]thiazolo[3,2-a]pyrimidine-2-carboxamide Chemical compound CCCCCCCCC1=CC=CC=C1NC(=O)C(S1)=C(O)N2C1=NCCC2 VXORTRSCEMECGR-UHFFFAOYSA-N 0.000 description 1
SWXMFHCXWGPHEU-UHFFFAOYSA-N 3-methoxy-n-(2-octylphenyl)-6,7-dihydro-5h-[1,3]thiazolo[3,2-a]pyrimidine-2-carboxamide Chemical compound CCCCCCCCC1=CC=CC=C1NC(=O)C(S1)=C(OC)N2C1=NCCC2 SWXMFHCXWGPHEU-UHFFFAOYSA-N 0.000 description 1
FJTAQHFINADDSR-UHFFFAOYSA-N 3-methyl-N-(2-pyrrolidin-1-ylethyl)-6,7-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-2-carboxamide dihydrochloride Chemical compound Cl.Cl.CC1=C(SC=2N1CCCN2)C(=O)NCCN2CCCC2 FJTAQHFINADDSR-UHFFFAOYSA-N 0.000 description 1
QONURZSLVGFWKJ-UHFFFAOYSA-N 3-methyl-n-(1,3-thiazol-2-yl)-6,7-dihydro-5h-[1,3]thiazolo[3,2-a]pyrimidine-2-carboxamide;hydrochloride Chemical compound Cl.S1C2=NCCCN2C(C)=C1C(=O)NC1=NC=CS1 QONURZSLVGFWKJ-UHFFFAOYSA-N 0.000 description 1
HMVCBJPSPBBSRF-UHFFFAOYSA-N 3-methyl-n-(2,4,4-trimethylpentan-2-yl)-6,7-dihydro-5h-[1,3]thiazolo[3,2-a]pyrimidine-2-carboxamide;hydrochloride Chemical compound Cl.C1CCN2C(C)=C(C(=O)NC(C)(C)CC(C)(C)C)SC2=N1 HMVCBJPSPBBSRF-UHFFFAOYSA-N 0.000 description 1
SSDUQULVLLUMOP-UHFFFAOYSA-N 3-methyl-n-(2-morpholin-4-ylethyl)-6,7-dihydro-5h-[1,3]thiazolo[3,2-a]pyrimidine-2-carboxamide;dihydrochloride Chemical compound Cl.Cl.S1C2=NCCCN2C(C)=C1C(=O)NCCN1CCOCC1 SSDUQULVLLUMOP-UHFFFAOYSA-N 0.000 description 1
MMMJJRRXUBTZQD-UHFFFAOYSA-N 3-methyl-n-(4-methylphenyl)-6,7-dihydro-5h-[1,3]thiazolo[3,2-a]pyrimidine-2-carboxamide;hydrochloride Chemical compound Cl.S1C2=NCCCN2C(C)=C1C(=O)NC1=CC=C(C)C=C1 MMMJJRRXUBTZQD-UHFFFAOYSA-N 0.000 description 1
ZGODIWWYZRIEPB-UHFFFAOYSA-N 3-methyl-n-(4-propylphenyl)-6,7-dihydro-5h-[1,3]thiazolo[3,2-a]pyrimidine-2-carboxamide;hydrochloride Chemical compound Cl.C1=CC(CCC)=CC=C1NC(=O)C(S1)=C(C)N2C1=NCCC2 ZGODIWWYZRIEPB-UHFFFAOYSA-N 0.000 description 1
LVPAANWRZYNVTJ-UHFFFAOYSA-N 3-methyl-n-octadecyl-6,7-dihydro-5h-[1,3]thiazolo[3,2-a]pyrimidine-2-carboxamide;hydrochloride Chemical compound Cl.C1CCN=C2SC(C(=O)NCCCCCCCCCCCCCCCCCC)=C(C)N21 LVPAANWRZYNVTJ-UHFFFAOYSA-N 0.000 description 1
MZSDPSUKPPTTQA-UHFFFAOYSA-N 3-methyl-n-octyl-6,7-dihydro-5h-[1,3]thiazolo[3,2-a]pyrimidine-2-carboxamide;hydrochloride Chemical compound Cl.C1CCN=C2SC(C(=O)NCCCCCCCC)=C(C)N21 MZSDPSUKPPTTQA-UHFFFAOYSA-N 0.000 description 1
ZNRGSYUVFVNSAW-UHFFFAOYSA-N 3-nitrophenylboronic acid Chemical compound OB(O)C1=CC=CC([N+]([O-])=O)=C1 ZNRGSYUVFVNSAW-UHFFFAOYSA-N 0.000 description 1
WRTZJHOCOJLJAB-UHFFFAOYSA-N 3-propyl-n-(4-propylphenyl)-6,7-dihydro-5h-[1,3]thiazolo[3,2-a]pyrimidine-2-carboxamide;hydrochloride Chemical compound Cl.S1C2=NCCCN2C(CCC)=C1C(=O)NC1=CC=C(CCC)C=C1 WRTZJHOCOJLJAB-UHFFFAOYSA-N 0.000 description 1
QOWSWEBLNVACCL-UHFFFAOYSA-N 4-Bromophenyl acetate Chemical compound OC(=O)CC1=CC=C(Br)C=C1 QOWSWEBLNVACCL-UHFFFAOYSA-N 0.000 description 1
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JYGCLUDTQZWGNJ-UHFFFAOYSA-N n-(3,5-dichlorophenyl)-3-propan-2-yl-6,7-dihydro-5h-[1,3]thiazolo[3,2-a]pyrimidine-2-carboxamide;hydrochloride Chemical compound Cl.S1C2=NCCCN2C(C(C)C)=C1C(=O)NC1=CC(Cl)=CC(Cl)=C1 JYGCLUDTQZWGNJ-UHFFFAOYSA-N 0.000 description 1
HMVQAGRJELMSKE-UHFFFAOYSA-N n-(3,5-dichlorophenyl)-3-propyl-6,7-dihydro-5h-[1,3]thiazolo[3,2-a]pyrimidine-2-carboxamide;hydrochloride Chemical compound Cl.S1C2=NCCCN2C(CCC)=C1C(=O)NC1=CC(Cl)=CC(Cl)=C1 HMVQAGRJELMSKE-UHFFFAOYSA-N 0.000 description 1
MHVXRSXVEFLGDY-UHFFFAOYSA-N n-(3,5-dichlorophenyl)-3-tridecyl-6,7-dihydro-5h-[1,3]thiazolo[3,2-a]pyrimidine-2-carboxamide;hydrochloride Chemical compound Cl.S1C2=NCCCN2C(CCCCCCCCCCCCC)=C1C(=O)NC1=CC(Cl)=CC(Cl)=C1 MHVXRSXVEFLGDY-UHFFFAOYSA-N 0.000 description 1
BZHIFZLNDRZDSZ-UHFFFAOYSA-N n-(3,5-dichlorophenyl)-n-(2-hydroxyethyl)-3-propyl-6,7-dihydro-5h-[1,3]thiazolo[3,2-a]pyrimidine-2-carboxamide;hydrochloride Chemical compound Cl.S1C2=NCCCN2C(CCC)=C1C(=O)N(CCO)C1=CC(Cl)=CC(Cl)=C1 BZHIFZLNDRZDSZ-UHFFFAOYSA-N 0.000 description 1
DHWRFACMDLJDSB-UHFFFAOYSA-N n-(3,5-dichlorophenyl)-n-methyl-3-propyl-6,7-dihydro-5h-[1,3]thiazolo[3,2-a]pyrimidine-2-carboxamide;hydrochloride Chemical compound Cl.S1C2=NCCCN2C(CCC)=C1C(=O)N(C)C1=CC(Cl)=CC(Cl)=C1 DHWRFACMDLJDSB-UHFFFAOYSA-N 0.000 description 1
DVBWHYCHCYMFPU-UHFFFAOYSA-N n-(3,5-difluorophenyl)-3-ethyl-6,7-dihydro-5h-[1,3]thiazolo[3,2-a]pyrimidine-2-carboxamide;hydrochloride Chemical compound Cl.S1C2=NCCCN2C(CC)=C1C(=O)NC1=CC(F)=CC(F)=C1 DVBWHYCHCYMFPU-UHFFFAOYSA-N 0.000 description 1
WDRWBQSINVIUJL-UHFFFAOYSA-N n-(3,5-difluorophenyl)-3-methyl-6,7-dihydro-5h-[1,3]thiazolo[3,2-a]pyrimidine-2-carboxamide;hydrochloride Chemical compound Cl.S1C2=NCCCN2C(C)=C1C(=O)NC1=CC(F)=CC(F)=C1 WDRWBQSINVIUJL-UHFFFAOYSA-N 0.000 description 1
ZAGGMENOFJSGJJ-UHFFFAOYSA-N n-(3,5-dimethoxyphenyl)-3-propyl-6,7-dihydro-5h-[1,3]thiazolo[3,2-a]pyrimidine-2-carboxamide;hydrochloride Chemical compound Cl.S1C2=NCCCN2C(CCC)=C1C(=O)NC1=CC(OC)=CC(OC)=C1 ZAGGMENOFJSGJJ-UHFFFAOYSA-N 0.000 description 1
ZXZHEWJGUYXJRN-UHFFFAOYSA-N n-(3,5-dimethylphenyl)-3,6,6-trimethyl-5,7-dihydro-[1,3]thiazolo[3,2-a]pyrimidine-2-carboxamide;hydrochloride Chemical class Cl.S1C2=NCC(C)(C)CN2C(C)=C1C(=O)NC1=CC(C)=CC(C)=C1 ZXZHEWJGUYXJRN-UHFFFAOYSA-N 0.000 description 1
HHZRSWJVDITWCU-UHFFFAOYSA-N n-(3,5-dimethylphenyl)-3-methyl-6,7-dihydro-5h-[1,3]thiazolo[3,2-a]pyrimidine-2-carboxamide;hydrochloride Chemical compound Cl.S1C2=NCCCN2C(C)=C1C(=O)NC1=CC(C)=CC(C)=C1 HHZRSWJVDITWCU-UHFFFAOYSA-N 0.000 description 1
YSVGJDIIEUUMII-UHFFFAOYSA-N n-(4-bromophenyl)-3-methyl-6,7-dihydro-5h-[1,3]thiazolo[3,2-a]pyrimidine-2-carboxamide;hydrochloride Chemical compound Cl.S1C2=NCCCN2C(C)=C1C(=O)NC1=CC=C(Br)C=C1 YSVGJDIIEUUMII-UHFFFAOYSA-N 0.000 description 1
SXNBRBPJMCRENB-UHFFFAOYSA-N n-(4-butylphenyl)-3-methyl-6,7-dihydro-5h-[1,3]thiazolo[3,2-a]pyrimidine-2-carboxamide;hydrochloride Chemical compound Cl.C1=CC(CCCC)=CC=C1NC(=O)C(S1)=C(C)N2C1=NCCC2 SXNBRBPJMCRENB-UHFFFAOYSA-N 0.000 description 1
UBMISLPMBOLSDA-UHFFFAOYSA-N n-(4-butylphenyl)-3-propyl-6,7-dihydro-5h-[1,3]thiazolo[3,2-a]pyrimidine-2-carboxamide;hydrochloride Chemical compound Cl.C1=CC(CCCC)=CC=C1NC(=O)C(S1)=C(CCC)N2C1=NCCC2 UBMISLPMBOLSDA-UHFFFAOYSA-N 0.000 description 1
HBVKUPBGRDGUEV-UHFFFAOYSA-N n-(4-chlorophenyl)-3-methyl-6,7-dihydro-5h-[1,3]thiazolo[3,2-a]pyrimidine-2-carboxamide;hydrochloride Chemical compound Cl.S1C2=NCCCN2C(C)=C1C(=O)NC1=CC=C(Cl)C=C1 HBVKUPBGRDGUEV-UHFFFAOYSA-N 0.000 description 1
ADJSIOXVAYBCLT-UHFFFAOYSA-N n-(4-decylphenyl)-3-propyl-6,7-dihydro-5h-[1,3]thiazolo[3,2-a]pyrimidine-2-carboxamide;hydrochloride Chemical compound Cl.C1=CC(CCCCCCCCCC)=CC=C1NC(=O)C(S1)=C(CCC)N2C1=NCCC2 ADJSIOXVAYBCLT-UHFFFAOYSA-N 0.000 description 1
FUXXMPZIZKYKKC-UHFFFAOYSA-N n-(4-ethylphenyl)-3-methyl-6,7-dihydro-5h-[1,3]thiazolo[3,2-a]pyrimidine-2-carboxamide;hydrochloride Chemical compound Cl.C1=CC(CC)=CC=C1NC(=O)C(S1)=C(C)N2C1=NCCC2 FUXXMPZIZKYKKC-UHFFFAOYSA-N 0.000 description 1
NSGRRZVLSVYPRF-UHFFFAOYSA-N n-(4-heptoxyphenyl)-3-propyl-6,7-dihydro-5h-[1,3]thiazolo[3,2-a]pyrimidine-2-carboxamide;hydrochloride Chemical compound Cl.C1=CC(OCCCCCCC)=CC=C1NC(=O)C(S1)=C(CCC)N2C1=NCCC2 NSGRRZVLSVYPRF-UHFFFAOYSA-N 0.000 description 1
ILSCAKHZJSSMOV-UHFFFAOYSA-N n-(4-heptylsulfanylphenyl)-3-propyl-6,7-dihydro-5h-[1,3]thiazolo[3,2-a]pyrimidine-2-carboxamide;hydrochloride Chemical compound Cl.C1=CC(SCCCCCCC)=CC=C1NC(=O)C(S1)=C(CCC)N2C1=NCCC2 ILSCAKHZJSSMOV-UHFFFAOYSA-N 0.000 description 1
QCSKNLODIJICLC-UHFFFAOYSA-N n-(4-heptylsulfonylphenyl)-3-propyl-6,7-dihydro-5h-[1,3]thiazolo[3,2-a]pyrimidine-2-carboxamide;hydrochloride Chemical compound Cl.C1=CC(S(=O)(=O)CCCCCCC)=CC=C1NC(=O)C(S1)=C(CCC)N2C1=NCCC2 QCSKNLODIJICLC-UHFFFAOYSA-N 0.000 description 1
XRZJEAXXVXNDKH-UHFFFAOYSA-N n-(4-hexylphenyl)-3-propyl-6,7-dihydro-5h-[1,3]thiazolo[3,2-a]pyrimidine-2-carboxamide;hydrochloride Chemical compound Cl.C1=CC(CCCCCC)=CC=C1NC(=O)C(S1)=C(CCC)N2C1=NCCC2 XRZJEAXXVXNDKH-UHFFFAOYSA-N 0.000 description 1
GGNPTWUXPQKXPR-UHFFFAOYSA-N n-(4-methoxyphenyl)-3-propan-2-yl-6,7-dihydro-5h-[1,3]thiazolo[3,2-a]pyrimidine-2-carboxamide;hydrochloride Chemical compound Cl.C1=CC(OC)=CC=C1NC(=O)C(S1)=C(C(C)C)N2C1=NCCC2 GGNPTWUXPQKXPR-UHFFFAOYSA-N 0.000 description 1
OKPPSABNCWNFRA-UHFFFAOYSA-N n-(4-octylphenyl)-3-propyl-6,7-dihydro-5h-[1,3]thiazolo[3,2-a]pyrimidine-2-carboxamide;hydrochloride Chemical compound Cl.C1=CC(CCCCCCCC)=CC=C1NC(=O)C(S1)=C(CCC)N2C1=NCCC2 OKPPSABNCWNFRA-UHFFFAOYSA-N 0.000 description 1
OLBULGLMDJRUDV-UHFFFAOYSA-N n-(4-tert-butylphenyl)-3-propyl-6,7-dihydro-5h-[1,3]thiazolo[3,2-a]pyrimidine-2-carboxamide;hydrochloride Chemical compound Cl.S1C2=NCCCN2C(CCC)=C1C(=O)NC1=CC=C(C(C)(C)C)C=C1 OLBULGLMDJRUDV-UHFFFAOYSA-N 0.000 description 1
ZHYGOSOAMTXICH-UHFFFAOYSA-N n-[4-(2-butoxyethoxy)phenyl]-3-propyl-6,7-dihydro-5h-[1,3]thiazolo[3,2-a]pyrimidine-2-carboxamide;hydrochloride Chemical class Cl.C1=CC(OCCOCCCC)=CC=C1NC(=O)C(S1)=C(CCC)N2C1=NCCC2 ZHYGOSOAMTXICH-UHFFFAOYSA-N 0.000 description 1
QZLMHNGFQHIOHV-UHFFFAOYSA-N n-[4-(2-butoxyethylsulfonyl)phenyl]-3-propyl-6,7-dihydro-5h-[1,3]thiazolo[3,2-a]pyrimidine-2-carboxamide;hydrochloride Chemical compound Cl.C1=CC(S(=O)(=O)CCOCCCC)=CC=C1NC(=O)C(S1)=C(CCC)N2C1=NCCC2 QZLMHNGFQHIOHV-UHFFFAOYSA-N 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
GMYRVPYRAGSDAK-UHFFFAOYSA-N n-phenyl-3-propyl-6,7-dihydro-5h-[1,3]thiazolo[3,2-a]pyrimidine-2-carboxamide;hydrochloride Chemical compound Cl.S1C2=NCCCN2C(CCC)=C1C(=O)NC1=CC=CC=C1 GMYRVPYRAGSDAK-UHFFFAOYSA-N 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
230000003472 neutralizing effect Effects 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
239000002674 ointment Substances 0.000 description 1
239000006186 oral dosage form Substances 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Chemical group 0.000 description 1
NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
230000001575 pathological effect Effects 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
235000011007 phosphoric acid Nutrition 0.000 description 1
125000003386 piperidinyl group Chemical group 0.000 description 1
229920001282 polysaccharide Polymers 0.000 description 1
239000005017 polysaccharide Substances 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
239000000047 product Substances 0.000 description 1
230000000069 prophylactic effect Effects 0.000 description 1
229940048914 protamine Drugs 0.000 description 1
125000003373 pyrazinyl group Chemical group 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
125000000719 pyrrolidinyl group Chemical group 0.000 description 1
XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
OTNVGWMVOULBFZ-UHFFFAOYSA-N sodium;hydrochloride Chemical compound [Na].Cl OTNVGWMVOULBFZ-UHFFFAOYSA-N 0.000 description 1
239000007921 spray Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
150000003431 steroids Chemical class 0.000 description 1
229960002317 succinimide Drugs 0.000 description 1
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000003826 tablet Substances 0.000 description 1
ZSDZTGGFCHRJNT-UHFFFAOYSA-N tert-butyl 3,6,6-trimethyl-5,7-dihydro-[1,3]thiazolo[3,2-a]pyrimidine-2-carboxylate;hydrochloride Chemical compound Cl.C1C(C)(C)CN2C(C)=C(C(=O)OC(C)(C)C)SC2=N1 ZSDZTGGFCHRJNT-UHFFFAOYSA-N 0.000 description 1
FBQJFMPKQJOYKY-UHFFFAOYSA-N tert-butyl 3-(3-ethoxy-3-oxopropyl)-6,7-dihydro-5h-[1,3]thiazolo[3,2-a]pyrimidine-2-carboxylate;hydrochloride Chemical compound Cl.C1CCN2C(CCC(=O)OCC)=C(C(=O)OC(C)(C)C)SC2=N1 FBQJFMPKQJOYKY-UHFFFAOYSA-N 0.000 description 1
CXNJGKYBZNYERG-UHFFFAOYSA-N tert-butyl 4-[4-[(3-cyclobutyl-6,7-dihydro-5h-[1,3]thiazolo[3,2-a]pyrimidine-2-carbonyl)amino]phenyl]benzoate;hydrochloride Chemical compound Cl.C1=CC(C(=O)OC(C)(C)C)=CC=C1C(C=C1)=CC=C1NC(=O)C(SC1=NCCCN11)=C1C1CCC1 CXNJGKYBZNYERG-UHFFFAOYSA-N 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000001113 thiadiazolyl group Chemical group 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
UBBZKZRMWONRRS-UHFFFAOYSA-N thionyl dichloride hydrochloride Chemical compound Cl.ClS(Cl)=O UBBZKZRMWONRRS-UHFFFAOYSA-N 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CN94105279A 1993-04-01 1994-04-01 噻唑并嘧啶衍生物 Pending CN1100425A (zh)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
JP110877/93		1993-04-01
JP11087793		1993-04-01

Publications (1)

Publication Number	Publication Date
CN1100425A true CN1100425A (zh)	1995-03-22

Family

ID=14546967

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CN94105279A Pending CN1100425A (zh)	1993-04-01	1994-04-01	噻唑并嘧啶衍生物

Country Status (9)

Country	Link
US (1)	US5599813A (2)
EP (1)	EP0618208A1 (2)
CN (1)	CN1100425A (2)
AU (1)	AU672675B2 (2)
CA (1)	CA2120395A1 (2)
FI (1)	FI941487L (2)
NO (1)	NO941135L (2)
PH (1)	PH31256A (2)
TW (1)	TW272193B (2)

Cited By (1)

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CN103443107A (zh) *	2011-03-28	2013-12-11	弗·哈夫曼-拉罗切有限公司	噻唑并嘧啶化合物

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KR20000022532A (ko) *	1996-06-27	2000-04-25	오노 야꾸힝 고교 가부시키가이샤	아릴(설파이드, 설폭시드 및 설폰)유도체 및 이를 활성 성분으로 함유하는 약물
ATE276763T1 (de)	1998-07-13	2004-10-15	Univ Texas	Verwendung von antikörper gegen aminophospholipide zur krebsbehandlung
SI1107795T1 (en)	1998-09-04	2003-06-30	The Regents Of The University Of Michigan	Thiomolybdate associated with at least one carbohydrate, and its use for preventing or treating diseases characterized by aberrant vascularization, such as cancer, wet type macular degeneration, rheumatoid arthritis
US6930101B1 (en)	1999-05-17	2005-08-16	The Regents Of The University Of California	Thiazolopyrimidines useful as TNFα inhibitors
DE10112197A1 (de) *	2001-03-14	2002-09-19	Gruenenthal Gmbh	Substituierte Pyrazolo- und Thiazolopyrimidine
EP2357009A1 (en)	2002-07-15	2011-08-17	Board of Regents, The University of Texas System	Duramycin peptide binding to anionic phospholipids and aminophospholipids conjugates and their use in treating viral infections
ES2809302T3 (es)	2004-01-22	2021-03-03	Univ Miami	Formulaciones de coenzima Q10 para tratar tumores sólidos mediante administración intravenosa
KR20070064660A (ko)	2004-10-07	2007-06-21	베링거 인겔하임 인터내셔날 게엠베하	Ｐｉ３ 키나제
ES2572356T3 (es)	2007-11-09	2016-05-31	Peregrine Pharmaceuticals Inc	Composiciones de anticuerpos dirigidos contra VEGF y procedimientos
EP2633864A1 (en)	2008-07-25	2013-09-04	The Regents of the University of Colorado	Clip inhibitors and methods of modulating immune function
CN101899058B (zh) *	2010-05-24	2012-05-23	中国人民解放军第四军医大学	一种噻唑并嘧啶化合物及其制备方法和应用
EP3576726A1 (en)	2017-02-06	2019-12-11	Massachusetts Institute Of Technology	Methods and products related to glutaminase inhibitors

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JPS52106893A (en) *	1976-01-19	1977-09-07	Diamond Shamrock Corp	Antiiinflammation imidazothiazole and thiazolopyrimidine
FR2479831A1 (fr) *	1980-04-08	1981-10-09	Synthelabo	Derives de thiazole, leur preparation et leur application en therapeutique
PL129375B1 (en) *	1980-07-24	1984-05-31	Rhone Poulenc Ind	Process for preparing novel derivatives of 2,3,6,7-tetrahydro-thiazole-/3,2-a/-pyrimidin-5-one
US4347248A (en) *	1981-03-23	1982-08-31	American Cyanamid Company	2,3-Disubstituted-thiazolo[3,2-a]pyrimidines
US5082838A (en) *	1989-06-21	1992-01-21	Takeda Chemical Industries, Ltd.	Sulfur-containing fused pyrimidine derivatives, their production and use

1994
- 1994-03-28 NO NO941135A patent/NO941135L/no unknown
- 1994-03-30 FI FI941487A patent/FI941487L/fi unknown
- 1994-03-30 PH PH48022A patent/PH31256A/en unknown
- 1994-03-31 CA CA002120395A patent/CA2120395A1/en not_active Abandoned
- 1994-03-31 AU AU59252/94A patent/AU672675B2/en not_active Ceased
- 1994-04-01 US US08/221,577 patent/US5599813A/en not_active Expired - Fee Related
- 1994-04-01 TW TW083102874A patent/TW272193B/zh active
- 1994-04-01 CN CN94105279A patent/CN1100425A/zh active Pending
- 1994-04-05 EP EP94105256A patent/EP0618208A1/en not_active Withdrawn

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN103443107A (zh) *	2011-03-28	2013-12-11	弗·哈夫曼-拉罗切有限公司	噻唑并嘧啶化合物
CN103443107B (zh) *	2011-03-28	2016-04-20	弗·哈夫曼-拉罗切有限公司	噻唑并嘧啶化合物

Also Published As

Publication number	Publication date
FI941487A0 (fi)	1994-03-30
NO941135D0 (no)	1994-03-28
US5599813A (en)	1997-02-04
NO941135L (no)	1994-10-03
EP0618208A1 (en)	1994-10-05
TW272193B (2)	1996-03-11
FI941487A7 (fi)	1994-10-02
AU5925294A (en)	1994-10-06
FI941487L (fi)	1994-10-02
PH31256A (en)	1998-06-18
AU672675B2 (en)	1996-10-10
CA2120395A1 (en)	1994-10-02

Legal Events

Date	Code	Title
1995-03-22	C06	Publication
1995-03-22	PB01	Publication
1996-07-17	C10	Entry into substantive examination
1996-07-17	SE01	Entry into force of request for substantive examination
2000-01-12	C01	Deemed withdrawal of patent application (patent law 1993)
2000-01-12	WD01	Invention patent application deemed withdrawn after publication

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