JPH0519549B2 - - Google Patents

Info

Publication number: JPH0519549B2
Authority: JP; Japan
Prior art keywords: formula; hydrogen; carbon atoms; alkyl; chlorine
Prior art date: 1983-07-22
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 - Lifetime

Application number

JP59149802A

Other languages

English (en)

Japanese (ja)

Other versions

JPS6042367A (ja

Inventor

Hooru Hetsuson Deibitsudo

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.)

DEYUHON MERUKU PHARM CO ZA

Original Assignee

DEYUHON MERUKU PHARM CO ZA

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.)

1983-07-22

Filing date

1984-07-20

Publication date

1993-03-17

1984-07-20 Application filed by DEYUHON MERUKU PHARM CO ZA filed Critical DEYUHON MERUKU PHARM CO ZA

1985-03-06 Publication of JPS6042367A publication Critical patent/JPS6042367A/ja

1993-03-17 Publication of JPH0519549B2 publication Critical patent/JPH0519549B2/ja

Status Granted legal-status Critical Current

Links

229910052739 hydrogen Inorganic materials 0.000 claims description 94
239000001257 hydrogen Substances 0.000 claims description 94
125000004432 carbon atom Chemical group C* 0.000 claims description 76
150000001875 compounds Chemical class 0.000 claims description 69
150000002431 hydrogen Chemical class 0.000 claims description 56
125000000217 alkyl group Chemical group 0.000 claims description 40
229910052801 chlorine Inorganic materials 0.000 claims description 36
239000000460 chlorine Substances 0.000 claims description 36
229910052736 halogen Inorganic materials 0.000 claims description 35
150000002367 halogens Chemical class 0.000 claims description 35
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 34
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 34
239000002904 solvent Substances 0.000 claims description 28
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims description 27
229910052731 fluorine Inorganic materials 0.000 claims description 24
239000011737 fluorine Substances 0.000 claims description 24
238000000034 method Methods 0.000 claims description 24
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 23
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 22
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 22
229910052794 bromium Inorganic materials 0.000 claims description 22
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
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 claims description 18
239000011734 sodium Substances 0.000 claims description 18
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 18
239000002253 acid Substances 0.000 claims description 17
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 17
-1 chloro-6-fluoro-3-methyl-4-quinolinecarboxylic acid Chemical compound 0.000 claims description 16
JXDYKVIHCLTXOP-UHFFFAOYSA-N isatin Chemical compound C1=CC=C2C(=O)C(=O)NC2=C1 JXDYKVIHCLTXOP-UHFFFAOYSA-N 0.000 claims description 16
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 16
LOAUVZALPPNFOQ-UHFFFAOYSA-N quinaldic acid Chemical compound C1=CC=CC2=NC(C(=O)O)=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-N 0.000 claims description 16
229910052708 sodium Inorganic materials 0.000 claims description 16
150000003839 salts Chemical class 0.000 claims description 13
UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 12
229910052500 inorganic mineral Inorganic materials 0.000 claims description 11
239000011707 mineral Substances 0.000 claims description 11
125000003545 alkoxy group Chemical group 0.000 claims description 10
125000000753 cycloalkyl group Chemical group 0.000 claims description 9
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 9
159000000000 sodium salts Chemical class 0.000 claims description 8
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
239000011541 reaction mixture Substances 0.000 claims description 7
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
125000003342 alkenyl group Chemical group 0.000 claims description 5
125000004414 alkyl thio group Chemical group 0.000 claims description 5
150000001412 amines Chemical class 0.000 claims description 5
125000000392 cycloalkenyl group Chemical group 0.000 claims description 5
239000003937 drug carrier Substances 0.000 claims description 5
150000002576 ketones Chemical class 0.000 claims description 5
229910052760 oxygen Inorganic materials 0.000 claims description 5
239000008194 pharmaceutical composition Substances 0.000 claims description 5
150000003242 quaternary ammonium salts Chemical class 0.000 claims description 5
229910052717 sulfur Inorganic materials 0.000 claims description 5
239000004472 Lysine Substances 0.000 claims description 4
KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims description 4
125000003277 amino group Chemical group 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
239000003586 protic polar solvent Substances 0.000 claims description 4
OZHIYEINSCNALY-UHFFFAOYSA-N 1-aminobutan-1-ol Chemical compound CCCC(N)O OZHIYEINSCNALY-UHFFFAOYSA-N 0.000 claims description 3
PHEZJEYUWHETKO-UHFFFAOYSA-N brequinar Chemical compound N1=C2C=CC(F)=CC2=C(C(O)=O)C(C)=C1C(C=C1)=CC=C1C1=CC=CC=C1F PHEZJEYUWHETKO-UHFFFAOYSA-N 0.000 claims description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 3
229910052751 metal Inorganic materials 0.000 claims description 3
239000002184 metal Substances 0.000 claims description 3
150000003573 thiols Chemical class 0.000 claims description 3
ODIGIKRIUKFKHP-UHFFFAOYSA-N (n-propan-2-yloxycarbonylanilino) acetate Chemical compound CC(C)OC(=O)N(OC(C)=O)C1=CC=CC=C1 ODIGIKRIUKFKHP-UHFFFAOYSA-N 0.000 claims description 2
ODILYAYKQDDXJJ-UHFFFAOYSA-N 6-fluoro-3-methyl-2-(4-phenoxyphenyl)quinoline-4-carboxylic acid Chemical compound N1=C2C=CC(F)=CC2=C(C(O)=O)C(C)=C1C(C=C1)=CC=C1OC1=CC=CC=C1 ODILYAYKQDDXJJ-UHFFFAOYSA-N 0.000 claims description 2
238000010438 heat treatment Methods 0.000 claims description 2
229910000000 metal hydroxide Inorganic materials 0.000 claims description 2
229910044991 metal oxide Inorganic materials 0.000 claims description 2
150000004706 metal oxides Chemical class 0.000 claims description 2
125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 4
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
SORCXZNGEDCCHD-UHFFFAOYSA-N 2-fluoro-3-methylquinoline-4-carboxylic acid Chemical compound C1=CC=CC2=C(C(O)=O)C(C)=C(F)N=C21 SORCXZNGEDCCHD-UHFFFAOYSA-N 0.000 claims 1
230000000771 oncological effect Effects 0.000 claims 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 72
206010028980 Neoplasm Diseases 0.000 description 34
241000699670 Mus sp. Species 0.000 description 26
VQMSRUREDGBWKT-UHFFFAOYSA-N quinoline-4-carboxylic acid Chemical class C1=CC=C2C(C(=O)O)=CC=NC2=C1 VQMSRUREDGBWKT-UHFFFAOYSA-N 0.000 description 26
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
238000012360 testing method Methods 0.000 description 23
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 21
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 20
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
239000004480 active ingredient Substances 0.000 description 18
238000006243 chemical reaction Methods 0.000 description 17
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
239000007787 solid Substances 0.000 description 15
210000004027 cell Anatomy 0.000 description 13
239000000203 mixture Substances 0.000 description 13
239000000243 solution Substances 0.000 description 12
230000004083 survival effect Effects 0.000 description 12
239000002244 precipitate Substances 0.000 description 10
238000010992 reflux Methods 0.000 description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
208000029742 colonic neoplasm Diseases 0.000 description 9
229940079593 drug Drugs 0.000 description 9
239000003814 drug Substances 0.000 description 9
238000011282 treatment Methods 0.000 description 9
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
241000699666 Mus <mouse, genus> Species 0.000 description 8
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
230000000259 anti-tumor effect Effects 0.000 description 7
230000002401 inhibitory effect Effects 0.000 description 7
235000010755 mineral Nutrition 0.000 description 7
230000004614 tumor growth Effects 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
229940111121 antirheumatic drug quinolines Drugs 0.000 description 6
230000000694 effects Effects 0.000 description 6
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
150000003248 quinolines Chemical class 0.000 description 6
YTRMTPPVNRALON-UHFFFAOYSA-N 2-phenyl-4-quinolinecarboxylic acid Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=CC=C1 YTRMTPPVNRALON-UHFFFAOYSA-N 0.000 description 5
238000009835 boiling Methods 0.000 description 5
239000002775 capsule Substances 0.000 description 5
239000011780 sodium chloride Substances 0.000 description 5
239000003826 tablet Substances 0.000 description 5
229920002153 Hydroxypropyl cellulose Polymers 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
229960000583 acetic acid Drugs 0.000 description 4
125000003118 aryl group Chemical group 0.000 description 4
230000037396 body weight Effects 0.000 description 4
ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 4
238000000354 decomposition reaction Methods 0.000 description 4
150000002148 esters Chemical class 0.000 description 4
239000001863 hydroxypropyl cellulose Substances 0.000 description 4
235000010977 hydroxypropyl cellulose Nutrition 0.000 description 4
239000007924 injection Substances 0.000 description 4
238000002347 injection Methods 0.000 description 4
238000011081 inoculation Methods 0.000 description 4
239000000543 intermediate Substances 0.000 description 4
201000001441 melanoma Diseases 0.000 description 4
230000000684 melanotic effect Effects 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
238000003756 stirring Methods 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
WYKKHJQZENLZID-UHFFFAOYSA-N 6-fluoro-3-methyl-2-(4-phenylphenyl)quinoline-4-carboxylic acid Chemical compound N1=C2C=CC(F)=CC2=C(C(O)=O)C(C)=C1C(C=C1)=CC=C1C1=CC=CC=C1 WYKKHJQZENLZID-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
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 3
241000124008 Mammalia Species 0.000 description 3
241001465754 Metazoa Species 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
230000015572 biosynthetic process Effects 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
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
239000007903 gelatin capsule Substances 0.000 description 3
239000012362 glacial acetic acid Substances 0.000 description 3
230000012010 growth Effects 0.000 description 3
239000012442 inert solvent Substances 0.000 description 3
230000005764 inhibitory process Effects 0.000 description 3
239000008101 lactose Substances 0.000 description 3
208000032839 leukemia Diseases 0.000 description 3
239000008297 liquid dosage form Substances 0.000 description 3
235000019359 magnesium stearate Nutrition 0.000 description 3
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
239000000047 product Substances 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
125000001424 substituent group Chemical group 0.000 description 3
239000000725 suspension Substances 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
JMBGDQSXJHLFTO-UHFFFAOYSA-N 1-(4-phenylphenyl)propan-1-one Chemical compound C1=CC(C(=O)CC)=CC=C1C1=CC=CC=C1 JMBGDQSXJHLFTO-UHFFFAOYSA-N 0.000 description 2
JIPUGCBCIYYRSB-UHFFFAOYSA-N 3-phenylquinoline-2-carboxylic acid Chemical class OC(=O)C1=NC2=CC=CC=C2C=C1C1=CC=CC=C1 JIPUGCBCIYYRSB-UHFFFAOYSA-N 0.000 description 2
GKODDAXOSGGARJ-UHFFFAOYSA-N 5-Fluoroisatin Chemical compound FC1=CC=C2NC(=O)C(=O)C2=C1 GKODDAXOSGGARJ-UHFFFAOYSA-N 0.000 description 2
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
239000004215 Carbon black (E152) Substances 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
206010009944 Colon cancer Diseases 0.000 description 2
GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 description 2
241000282412 Homo Species 0.000 description 2
208000028018 Lymphocytic leukaemia Diseases 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
230000000078 anti-malarial effect Effects 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
239000000969 carrier Substances 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
125000001309 chloro group Chemical group Cl* 0.000 description 2
OSASVXMJTNOKOY-UHFFFAOYSA-N chlorobutanol Chemical compound CC(C)(O)C(Cl)(Cl)Cl OSASVXMJTNOKOY-UHFFFAOYSA-N 0.000 description 2
DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 description 2
229960004316 cisplatin Drugs 0.000 description 2
238000000576 coating method Methods 0.000 description 2
210000001072 colon Anatomy 0.000 description 2
201000010897 colon adenocarcinoma Diseases 0.000 description 2
239000007891 compressed tablet Substances 0.000 description 2
239000002552 dosage form Substances 0.000 description 2
125000004494 ethyl ester group Chemical group 0.000 description 2
238000011156 evaluation Methods 0.000 description 2
229960002949 fluorouracil Drugs 0.000 description 2
125000000623 heterocyclic group Chemical group 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
150000002430 hydrocarbons Chemical class 0.000 description 2
150000002440 hydroxy compounds Chemical class 0.000 description 2
238000000338 in vitro Methods 0.000 description 2
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
208000003747 lymphoid leukemia Diseases 0.000 description 2
239000000463 material Substances 0.000 description 2
238000010907 mechanical stirring Methods 0.000 description 2
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
239000003182 parenteral nutrition solution Substances 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
239000003381 stabilizer Substances 0.000 description 2
UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 2
239000007929 subcutaneous injection Substances 0.000 description 2
238000010254 subcutaneous injection Methods 0.000 description 2
239000012730 sustained-release form Substances 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
210000001519 tissue Anatomy 0.000 description 2
CSRZQMIRAZTJOY-UHFFFAOYSA-N trimethylsilyl iodide Chemical compound C[Si](C)(C)I CSRZQMIRAZTJOY-UHFFFAOYSA-N 0.000 description 2
210000004881 tumor cell Anatomy 0.000 description 2
239000003981 vehicle Substances 0.000 description 2
XDIYNQZUNSSENW-UUBOPVPUSA-N (2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O XDIYNQZUNSSENW-UUBOPVPUSA-N 0.000 description 1
ZXIQZWXVSBJPTC-UHFFFAOYSA-N 1-[4-(2-fluorophenyl)phenyl]propan-1-one Chemical compound C1=CC(C(=O)CC)=CC=C1C1=CC=CC=C1F ZXIQZWXVSBJPTC-UHFFFAOYSA-N 0.000 description 1
KODLUXHSIZOKTG-UHFFFAOYSA-N 1-aminobutan-2-ol Chemical compound CCC(O)CN KODLUXHSIZOKTG-UHFFFAOYSA-N 0.000 description 1
INPQMFGLMYDYCM-UHFFFAOYSA-N 2-(4-chlorophenyl)-6-fluoroquinoline-4-carboxylic acid Chemical compound N=1C2=CC=C(F)C=C2C(C(=O)O)=CC=1C1=CC=C(Cl)C=C1 INPQMFGLMYDYCM-UHFFFAOYSA-N 0.000 description 1
GBGDJTGJJQHTCJ-UHFFFAOYSA-N 2-(4-cyclohexylphenyl)-6-fluoro-3-methylquinoline-4-carboxylic acid Chemical compound N1=C2C=CC(F)=CC2=C(C(O)=O)C(C)=C1C(C=C1)=CC=C1C1CCCCC1 GBGDJTGJJQHTCJ-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
IILALAZIKXQFSK-UHFFFAOYSA-N 2-[4-(4-bromophenyl)phenyl]-6-fluoro-3-methylquinoline-4-carboxylic acid Chemical compound N1=C2C=CC(F)=CC2=C(C(O)=O)C(C)=C1C(C=C1)=CC=C1C1=CC=C(Br)C=C1 IILALAZIKXQFSK-UHFFFAOYSA-N 0.000 description 1
DRHIRYPNSWWCKG-UHFFFAOYSA-N 2-cyclohexyl-1-phenylpropan-1-one Chemical compound C=1C=CC=CC=1C(=O)C(C)C1CCCCC1 DRHIRYPNSWWCKG-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
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239000011248 coating agent Substances 0.000 description 1
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238000004040 coloring Methods 0.000 description 1
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150000004820 halides Chemical class 0.000 description 1
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239000002198 insoluble material Substances 0.000 description 1
239000007928 intraperitoneal injection Substances 0.000 description 1
125000002346 iodo group Chemical group I* 0.000 description 1
210000004185 liver Anatomy 0.000 description 1
210000005228 liver tissue Anatomy 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
239000002609 medium Substances 0.000 description 1
235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
235000019813 microcrystalline cellulose Nutrition 0.000 description 1
239000008108 microcrystalline cellulose Substances 0.000 description 1
229940016286 microcrystalline cellulose Drugs 0.000 description 1
PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
239000003921 oil Substances 0.000 description 1
235000019198 oils Nutrition 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
229960003540 oxyquinoline Drugs 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
229940049954 penicillin Drugs 0.000 description 1
230000003285 pharmacodynamic effect Effects 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
229920000053 polysorbate 80 Polymers 0.000 description 1
230000008092 positive effect Effects 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
CHWRSCGUEQEHOH-UHFFFAOYSA-N potassium oxide Chemical compound [O-2].[K+].[K+] CHWRSCGUEQEHOH-UHFFFAOYSA-N 0.000 description 1
229910001950 potassium oxide Inorganic materials 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
KXYNLLGPBDUAHW-UHFFFAOYSA-N quinolin-4-ylmethanol Chemical compound C1=CC=C2C(CO)=CC=NC2=C1 KXYNLLGPBDUAHW-UHFFFAOYSA-N 0.000 description 1
MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
230000005855 radiation Effects 0.000 description 1
WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
235000010234 sodium benzoate Nutrition 0.000 description 1
239000004299 sodium benzoate Substances 0.000 description 1
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
229910001948 sodium oxide Inorganic materials 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
235000010265 sodium sulphite Nutrition 0.000 description 1
ALMGTSDIZUJBKG-UHFFFAOYSA-M sodium;5-chloro-6-fluoro-3-methyl-2-(4-phenylphenyl)quinoline-4-carboxylate Chemical compound [Na+].N1=C2C=CC(F)=C(Cl)C2=C(C([O-])=O)C(C)=C1C(C=C1)=CC=C1C1=CC=CC=C1 ALMGTSDIZUJBKG-UHFFFAOYSA-M 0.000 description 1
HQEDWSSKRPKZLL-UHFFFAOYSA-M sodium;6-fluoro-3-methyl-2-(4-phenylphenyl)quinoline-4-carboxylate Chemical compound [Na+].N1=C2C=CC(F)=CC2=C(C([O-])=O)C(C)=C1C(C=C1)=CC=C1C1=CC=CC=C1 HQEDWSSKRPKZLL-UHFFFAOYSA-M 0.000 description 1
239000007909 solid dosage form Substances 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
235000012424 soybean oil Nutrition 0.000 description 1
239000003549 soybean oil Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
229960005322 streptomycin Drugs 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
229940124530 sulfonamide Drugs 0.000 description 1
150000003456 sulfonamides Chemical class 0.000 description 1
150000003462 sulfoxides Chemical class 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
238000001356 surgical procedure Methods 0.000 description 1
238000013268 sustained release Methods 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
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
238000010998 test method Methods 0.000 description 1
UEUXEKPTXMALOB-UHFFFAOYSA-J tetrasodium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O UEUXEKPTXMALOB-UHFFFAOYSA-J 0.000 description 1
150000007944 thiolates Chemical class 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000009466 transformation Effects 0.000 description 1
239000012588 trypsin Substances 0.000 description 1
230000002100 tumorsuppressive effect Effects 0.000 description 1
MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
235000012141 vanillin Nutrition 0.000 description 1
238000005406 washing Methods 0.000 description 1
238000005303 weighing Methods 0.000 description 1

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Plural Heterocyclic Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

JP59149802A 1983-07-22 1984-07-20 抗腫瘍剤としてのフエニルキノリンカルボン酸および誘導体 Granted JPS6042367A (ja)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date
US51631983A	1983-07-22	1983-07-22
US516319		1983-07-22
US605104		1984-04-30

Publications (2)

Publication Number	Publication Date
JPS6042367A JPS6042367A (ja)	1985-03-06
JPH0519549B2 true JPH0519549B2 (es)	1993-03-17

Family

ID=24055041

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP59149802A Granted JPS6042367A (ja)	1983-07-22	1984-07-20	抗腫瘍剤としてのフエニルキノリンカルボン酸および誘導体

Country Status (2)

Country	Link
JP (1)	JPS6042367A (es)
ZA (1)	ZA845594B (es)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4847381A (en) *	1987-08-31	1989-07-11	American Cyanamid Company	2-Phenyl-4-quinoline carboxylic acids
US7671065B2 (en) *	2005-02-24	2010-03-02	Janssen Pharmaceutica N.V.	Pyridine derivatives as potassium ion channel openers
WO2009016812A1 (ja) *	2007-07-27	2009-02-05	Kowa Company, Ltd.	２－フェニルキノリン－４－カルボン酸誘導体を有効成分とする貧血の予防及び／又は治療剤
CA2898615A1 (en) *	2013-01-28	2014-07-31	Viamet Pharmaceuticals, Inc.	Metalloenzyme inhibitor compounds
US8927717B1 (en) *	2014-02-14	2015-01-06	National Defense Medical Center	Thiochromeno[2,3-c]quinolin-12-one derivatives, preparation method and application thereof
AU2019242628A1 (en) *	2018-03-26	2020-09-24	Clear Creek Bio, Inc.	Compositions and methods for inhibiting dihydroorotate dehydrogenase

1984
- 1984-07-19 ZA ZA845594A patent/ZA845594B/xx unknown
- 1984-07-20 JP JP59149802A patent/JPS6042367A/ja active Granted

Also Published As

Publication number	Publication date
ZA845594B (en)	1986-03-26
JPS6042367A (ja)	1985-03-06

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