TW299322B - - Google Patents

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Publication number: TW299322B
Authority: TW; Taiwan
Prior art keywords: formula; compound; group; hydrogen; alkyl
Prior art date: 1991-01-14

Application number

TW080109989A

Other languages

English (en)

Chinese (zh)

Original Assignee

Ciba Geigy Ag

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.)

1991-01-14

Filing date

1991-12-20

Publication date

1997-03-01

1991-12-20 Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag

1997-03-01 Application granted granted Critical

1997-03-01 Publication of TW299322B publication Critical patent/TW299322B/zh

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150000001875 compounds Chemical class 0.000 claims description 124
125000000217 alkyl group Chemical group 0.000 claims description 48
150000003839 salts Chemical class 0.000 claims description 42
229910052717 sulfur Inorganic materials 0.000 claims description 25
238000011049 filling Methods 0.000 claims description 22
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 19
239000001257 hydrogen Substances 0.000 claims description 18
229910052739 hydrogen Inorganic materials 0.000 claims description 18
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
239000008194 pharmaceutical composition Substances 0.000 claims description 5
208000010362 Protozoan Infections Diseases 0.000 claims description 2
239000003937 drug carrier Substances 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims 2
ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 claims 1
-1 hexahydropyridyl Chemical group 0.000 description 43
239000000203 mixture Substances 0.000 description 29
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 27
238000012360 testing method Methods 0.000 description 25
239000007789 gas Substances 0.000 description 22
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
238000006243 chemical reaction Methods 0.000 description 19
150000001335 aliphatic alkanes Chemical group 0.000 description 18
239000000243 solution Substances 0.000 description 18
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 17
238000000034 method Methods 0.000 description 17
125000002947 alkylene group Chemical group 0.000 description 16
239000004480 active ingredient Substances 0.000 description 15
239000002253 acid Substances 0.000 description 14
239000000126 substance Substances 0.000 description 13
239000003814 drug Substances 0.000 description 11
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
229940079593 drug Drugs 0.000 description 10
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
102000005758 Adenosylmethionine decarboxylase Human genes 0.000 description 9
108010070753 Adenosylmethionine decarboxylase Proteins 0.000 description 9
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 9
125000003277 amino group Chemical class 0.000 description 9
239000003795 chemical substances by application Substances 0.000 description 9
125000004435 hydrogen atom Chemical class [H]* 0.000 description 9
239000000543 intermediate Substances 0.000 description 9
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 9
201000002311 trypanosomiasis Diseases 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 8
125000003282 alkyl amino group Chemical group 0.000 description 8
150000001409 amidines Chemical class 0.000 description 8
150000001412 amines Chemical class 0.000 description 8
238000002309 gasification Methods 0.000 description 8
239000002904 solvent Substances 0.000 description 8
239000007858 starting material Substances 0.000 description 8
125000001424 substituent group Chemical group 0.000 description 8
125000003118 aryl group Chemical group 0.000 description 7
230000000875 corresponding effect Effects 0.000 description 7
230000000694 effects Effects 0.000 description 7
229910052736 halogen Inorganic materials 0.000 description 7
150000002367 halogens Chemical class 0.000 description 7
230000005764 inhibitory process Effects 0.000 description 7
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
125000005907 alkyl ester group Chemical group 0.000 description 6
238000001816 cooling Methods 0.000 description 6
125000004093 cyano group Chemical group *C#N 0.000 description 6
230000002401 inhibitory effect Effects 0.000 description 6
238000002360 preparation method Methods 0.000 description 6
150000003254 radicals Chemical class 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
229910021529 ammonia Inorganic materials 0.000 description 5
239000002775 capsule Substances 0.000 description 5
230000002079 cooperative effect Effects 0.000 description 5
239000007788 liquid Substances 0.000 description 5
239000002609 medium Substances 0.000 description 5
150000002825 nitriles Chemical class 0.000 description 5
229920000768 polyamine Polymers 0.000 description 5
238000010992 reflux Methods 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
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 4
239000002202 Polyethylene glycol Substances 0.000 description 4
229920002472 Starch Polymers 0.000 description 4
IWLBIFVMPLUHLK-UHFFFAOYSA-N azane;formaldehyde Chemical compound N.O=C IWLBIFVMPLUHLK-UHFFFAOYSA-N 0.000 description 4
210000004027 cell Anatomy 0.000 description 4
KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 4
239000003153 chemical reaction reagent Substances 0.000 description 4
201000010099 disease Diseases 0.000 description 4
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Natural products O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
238000007911 parenteral administration Methods 0.000 description 4
239000000546 pharmaceutical excipient Substances 0.000 description 4
229920001223 polyethylene glycol Polymers 0.000 description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
239000011734 sodium Substances 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
239000011593 sulfur Substances 0.000 description 4
239000000454 talc Substances 0.000 description 4
229910052623 talc Inorganic materials 0.000 description 4
235000012222 talc Nutrition 0.000 description 4
229910052720 vanadium Inorganic materials 0.000 description 4
KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 3
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical group CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 3
XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
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 3
239000001888 Peptone Substances 0.000 description 3
108010080698 Peptones Proteins 0.000 description 3
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 3
BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
125000003545 alkoxy group Chemical group 0.000 description 3
150000003973 alkyl amines Chemical class 0.000 description 3
125000004448 alkyl carbonyl group Chemical group 0.000 description 3
238000005804 alkylation reaction Methods 0.000 description 3
239000012298 atmosphere Substances 0.000 description 3
238000009835 boiling Methods 0.000 description 3
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
230000008859 change Effects 0.000 description 3
125000000753 cycloalkyl group Chemical group 0.000 description 3
239000003085 diluting agent Substances 0.000 description 3
239000002552 dosage form Substances 0.000 description 3
239000008103 glucose Substances 0.000 description 3
230000012010 growth Effects 0.000 description 3
125000005842 heteroatom Chemical group 0.000 description 3
230000007062 hydrolysis Effects 0.000 description 3
238000006460 hydrolysis reaction Methods 0.000 description 3
FDGQSTZJBFJUBT-UHFFFAOYSA-N hypoxanthine Chemical compound O=C1NC=NC2=C1NC=N2 FDGQSTZJBFJUBT-UHFFFAOYSA-N 0.000 description 3
238000000338 in vitro Methods 0.000 description 3
238000011534 incubation Methods 0.000 description 3
239000004615 ingredient Substances 0.000 description 3
239000003112 inhibitor Substances 0.000 description 3
239000007937 lozenge Substances 0.000 description 3
239000011777 magnesium Substances 0.000 description 3
229910052749 magnesium Inorganic materials 0.000 description 3
239000000463 material Substances 0.000 description 3
230000002503 metabolic effect Effects 0.000 description 3
235000019319 peptone Nutrition 0.000 description 3
238000007639 printing Methods 0.000 description 3
230000009467 reduction Effects 0.000 description 3
230000002829 reductive effect Effects 0.000 description 3
150000003335 secondary amines Chemical class 0.000 description 3
229910052709 silver Inorganic materials 0.000 description 3
239000004332 silver Substances 0.000 description 3
239000003381 stabilizer Substances 0.000 description 3
239000008107 starch Substances 0.000 description 3
235000019698 starch Nutrition 0.000 description 3
235000000346 sugar Nutrition 0.000 description 3
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 2
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
102000004190 Enzymes Human genes 0.000 description 2
108090000790 Enzymes Proteins 0.000 description 2
OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 2
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
239000005977 Ethylene Substances 0.000 description 2
241000282326 Felis catus Species 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
CEAZRRDELHUEMR-URQXQFDESA-N Gentamicin Chemical compound O1[C@H](C(C)NC)CC[C@@H](N)[C@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](NC)[C@@](C)(O)CO2)O)[C@H](N)C[C@@H]1N CEAZRRDELHUEMR-URQXQFDESA-N 0.000 description 2
229930182566 Gentamicin Natural products 0.000 description 2
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 2
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 2
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
229930195725 Mannitol Natural products 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
DLRVVLDZNNYCBX-UHFFFAOYSA-N Polydextrose Polymers OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(O)O1 DLRVVLDZNNYCBX-UHFFFAOYSA-N 0.000 description 2
MEFKEPWMEQBLKI-AIRLBKTGSA-N S-adenosyl-L-methioninate Chemical compound O[C@@H]1[C@H](O)[C@@H](C[S+](CC[C@H](N)C([O-])=O)C)O[C@H]1N1C2=NC=NC(N)=C2N=C1 MEFKEPWMEQBLKI-AIRLBKTGSA-N 0.000 description 2
240000004808 Saccharomyces cerevisiae Species 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
JZRWCGZRTZMZEH-UHFFFAOYSA-N Thiamine Natural products CC1=C(CCO)SC=[N+]1CC1=CN=C(C)N=C1N JZRWCGZRTZMZEH-UHFFFAOYSA-N 0.000 description 2
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
241000223104 Trypanosoma Species 0.000 description 2
240000008042 Zea mays Species 0.000 description 2
235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 2
235000002017 Zea mays subsp mays Nutrition 0.000 description 2
229960000583 acetic acid Drugs 0.000 description 2
KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
230000004913 activation Effects 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
150000001299 aldehydes Chemical class 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
150000001336 alkenes Chemical group 0.000 description 2
125000005153 alkyl sulfamoyl group Chemical group 0.000 description 2
230000029936 alkylation Effects 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
239000011230 binding agent Substances 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
230000017531 blood circulation Effects 0.000 description 2
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
239000011575 calcium Substances 0.000 description 2
150000001735 carboxylic acids Chemical class 0.000 description 2
239000000969 carrier Substances 0.000 description 2
239000011248 coating agent Substances 0.000 description 2
238000000576 coating method Methods 0.000 description 2
235000008504 concentrate Nutrition 0.000 description 2
239000012141 concentrate Substances 0.000 description 2
OPHUWKNKFYBPDR-UHFFFAOYSA-N copper lithium Chemical compound [Li].[Cu] OPHUWKNKFYBPDR-UHFFFAOYSA-N 0.000 description 2
230000008878 coupling Effects 0.000 description 2
238000010168 coupling process Methods 0.000 description 2
238000005859 coupling reaction Methods 0.000 description 2
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
239000000945 filler Substances 0.000 description 2
235000019253 formic acid Nutrition 0.000 description 2
239000007903 gelatin capsule Substances 0.000 description 2
239000011521 glass Substances 0.000 description 2
125000005843 halogen group Chemical group 0.000 description 2
229910000037 hydrogen sulfide Inorganic materials 0.000 description 2
238000011081 inoculation Methods 0.000 description 2
239000002198 insoluble material Substances 0.000 description 2
229910052740 iodine Inorganic materials 0.000 description 2
239000008101 lactose Substances 0.000 description 2
229910052744 lithium Inorganic materials 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
235000009973 maize Nutrition 0.000 description 2
239000000594 mannitol Substances 0.000 description 2
235000010355 mannitol Nutrition 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
125000000449 nitro group Chemical class [O-][N+](*)=O 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
231100000252 nontoxic Toxicity 0.000 description 2
230000003000 nontoxic effect Effects 0.000 description 2
239000008203 oral pharmaceutical composition Substances 0.000 description 2
239000003791 organic solvent mixture Substances 0.000 description 2
238000003359 percent control normalization Methods 0.000 description 2
229920000137 polyphosphoric acid Polymers 0.000 description 2
239000000843 powder Substances 0.000 description 2
150000003141 primary amines Chemical class 0.000 description 2
239000000047 product Substances 0.000 description 2
KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 2
SYUHGPGVQRZVTB-UHFFFAOYSA-N radon atom Chemical group [Rn] SYUHGPGVQRZVTB-UHFFFAOYSA-N 0.000 description 2
230000035945 sensitivity Effects 0.000 description 2
210000002966 serum Anatomy 0.000 description 2
VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 2
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
238000006467 substitution reaction Methods 0.000 description 2
125000000542 sulfonic acid group Chemical group 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
235000019157 thiamine Nutrition 0.000 description 2
229960003495 thiamine Drugs 0.000 description 2
239000011721 thiamine Substances 0.000 description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
238000005160 1H NMR spectroscopy Methods 0.000 description 1
FJJYHTVHBVXEEQ-UHFFFAOYSA-N 2,2-dimethylpropanal Chemical group CC(C)(C)C=O FJJYHTVHBVXEEQ-UHFFFAOYSA-N 0.000 description 1
JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 1
ZFFBIQMNKOJDJE-UHFFFAOYSA-N 2-bromo-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(Br)C(=O)C1=CC=CC=C1 ZFFBIQMNKOJDJE-UHFFFAOYSA-N 0.000 description 1
125000000143 2-carboxyethyl group Chemical group [H]OC(=O)C([H])([H])C([H])([H])* 0.000 description 1
125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
244000215068 Acacia senegal Species 0.000 description 1
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150000008163 sugars Chemical class 0.000 description 1
QXTCFDCJXWLNAP-UHFFFAOYSA-N sulfidonitrogen(.) Chemical compound S=[N] QXTCFDCJXWLNAP-UHFFFAOYSA-N 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000002511 suppository base Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
230000008961 swelling Effects 0.000 description 1
238000010998 test method Methods 0.000 description 1
238000005979 thermal decomposition reaction Methods 0.000 description 1
KYMBYSLLVAOCFI-UHFFFAOYSA-N thiamine Chemical compound CC1=C(CCO)SCN1CC1=CN=C(C)N=C1N KYMBYSLLVAOCFI-UHFFFAOYSA-N 0.000 description 1
BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical group C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
239000004408 titanium dioxide Substances 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
238000012546 transfer Methods 0.000 description 1
150000003626 triacylglycerols Chemical class 0.000 description 1
FDESXGYTJJWFNN-UHFFFAOYSA-H tricalcium oxalate Chemical compound [Ca++].[Ca++].[Ca++].[O-]C(=O)C([O-])=O.[O-]C(=O)C([O-])=O.[O-]C(=O)C([O-])=O FDESXGYTJJWFNN-UHFFFAOYSA-H 0.000 description 1
LEIMLDGFXIOXMT-UHFFFAOYSA-N trimethylsilyl cyanide Chemical compound C[Si](C)(C)C#N LEIMLDGFXIOXMT-UHFFFAOYSA-N 0.000 description 1
210000004881 tumor cell Anatomy 0.000 description 1
229910052721 tungsten Inorganic materials 0.000 description 1
239000005483 tyrosine kinase inhibitor Substances 0.000 description 1
238000002255 vaccination Methods 0.000 description 1
239000006200 vaporizer Substances 0.000 description 1
230000035899 viability Effects 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
230000003612 virological effect Effects 0.000 description 1
239000000341 volatile oil Substances 0.000 description 1
238000005303 weighing Methods 0.000 description 1
229940100445 wheat starch Drugs 0.000 description 1
229910052726 zirconium Inorganic materials 0.000 description 1

Classifications

- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

TW080109989A 1991-01-14 1991-12-20 TW299322B (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH8591491		1991-01-14

Publications (1)

Publication Number	Publication Date
TW299322B true TW299322B (fr)	1997-03-01

Family

ID=51565536

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
TW080109989A TW299322B (fr)	1991-01-14	1991-12-20

Country Status (2)

Country	Link
TN (1)	TNSN92001A1 (fr)
TW (1)	TW299322B (fr)

1991
- 1991-12-20 TW TW080109989A patent/TW299322B/zh active
1992
- 1992-01-13 TN TNTNSN92001A patent/TNSN92001A1/fr unknown

Also Published As

Publication number	Publication date
TNSN92001A1 (fr)	1993-06-08

Publication	Publication Date	Title
CA2349227C (fr)	2008-02-05	2-phenylbenzimidazoles substitues, leur preparation et leur utilisation
EP0335832B1 (fr)	1993-02-10	Arylhydrazones
Larsen et al.	2001	Synthesis and biological activity of analogues of the antidiabetic/antiobesity agent 3-guanidinopropionic acid: discovery of a novel aminoguanidinoacetic acid antidiabetic agent
KR20090023585A (ko)	2009-03-05	Ｇｓｋ-3 억제제로서의 ｎ-(2-티아졸릴)-아미드 유도체
CN106458868A (zh)	2017-02-22	胍化合物及其用途
BRPI0614805A2 (pt)	2011-04-12	poliaminas úteis como produtos terapêuticos antiparasìticos e anticáncer e como inibidores de demetilase lisina-especìficos
TW201111379A (en)	2011-04-01	Novel thiazole-and oxazole-hepcidine-antagonists
EP3222614A2 (fr)	2017-09-27	Composé de biguanide et utilisation de celui-ci
JPH0276843A (ja)	1990-03-16	ビアリール化合物及びその製造方法
US4039685A (en)	1977-08-02	1-phenoxy-2-hydroxy-3-tert.-butylamino propane antiarrhythmic compounds
Short et al.	1963	Sympathetic Nervous System Blocking Agents. Derivatives of Guanidine and Related Compounds1
CN114126651A (zh)	2022-03-01	对二肽重复蛋白的抑制
KR20010031803A (ko)	2001-04-16	Ｎｏｓ 저해작용을 갖는 복소환 화합물
JPH04210946A (ja)	1992-08-03	新規なアリールビニルアミド誘導体およびその製造方法
US7528259B2 (en)	2009-05-05	Derivatives of 4,5,6,7-tetrabromobenzimidazole and method of their preparation
CN100594211C (zh)	2010-03-17	4-甲氧基-1,3一苯二取代酰胺衍生物
AU648872B2 (en)	1994-05-05	Lipoxygenase-inhibiting hydroxamic acid and N-hydroxyurea derivatives
JPS63141955A (ja)	1988-06-14	トリベンジルアミン誘導体
HK1000919B (en)	1998-05-08	Hydrazones
GB1592380A (en)	1981-07-08	Pharmacologically-active benzenesulphonyl urea derivatives and pharmaceutical compositions thereof
US2891949A (en)	1959-06-23	Sulfapyrimidines and methods of preparing the same
KR100630291B1 (ko)	2006-09-29	((아미노이미노메틸)아미노)알칸카르복스아미드 및 이의치료법에서의 용도
JPH01165586A (ja)	1989-06-29	抗腫瘍プロドラッグ
US5354761A (en)	1994-10-11	Bipyridyls
US3632628A (en)	1972-01-04	Sulfonamidoalkyl amino acids