NO752174L - - Google Patents

Info

Publication number: NO752174L
Authority: NO; Norway
Prior art keywords: alkyl; compound; formula; physiologically tolerable; cycloalkyl
Prior art date: 1974-06-19

Application number

NO752174A

Other languages

English (en)

Norwegian (no)

Inventor

H A Albrecht

J T Plati

Original Assignee

Hoffmann La Roche

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.)

1974-06-19

Filing date

1975-06-18

Publication date

1975-12-22

1975-06-18 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

1975-12-22 Publication of NO752174L publication Critical patent/NO752174L/no

Links

150000001875 compounds Chemical class 0.000 claims description 55
239000000203 mixture Substances 0.000 claims description 45
-1 sulfanilamide alkali metal salt Chemical class 0.000 claims description 29
150000003839 salts Chemical class 0.000 claims description 25
229940124530 sulfonamide Drugs 0.000 claims description 22
229910052739 hydrogen Inorganic materials 0.000 claims description 16
239000001257 hydrogen Substances 0.000 claims description 16
239000002585 base Substances 0.000 claims description 14
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
238000000034 method Methods 0.000 claims description 12
238000002360 preparation method Methods 0.000 claims description 8
239000002253 acid Substances 0.000 claims description 7
125000002252 acyl group Chemical group 0.000 claims description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
239000007788 liquid Substances 0.000 claims description 5
229910052783 alkali metal Inorganic materials 0.000 claims description 4
125000003277 amino group Chemical group 0.000 claims description 4
230000000844 anti-bacterial effect Effects 0.000 claims description 4
239000000969 carrier Substances 0.000 claims description 4
238000002156 mixing Methods 0.000 claims description 4
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
230000002378 acidificating effect Effects 0.000 claims description 3
239000013543 active substance Substances 0.000 claims description 3
125000003545 alkoxy group Chemical group 0.000 claims description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
125000006239 protecting group Chemical group 0.000 claims description 3
239000007787 solid Substances 0.000 claims description 3
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
IEDVJHCEMCRBQM-UHFFFAOYSA-N trimethoprim Chemical group COC1=C(OC)C(OC)=CC(CC=2C(=NC(N)=NC=2)N)=C1 IEDVJHCEMCRBQM-UHFFFAOYSA-N 0.000 claims description 2
125000003282 alkyl amino group Chemical group 0.000 claims 2
125000000217 alkyl group Chemical group 0.000 claims 2
238000004519 manufacturing process Methods 0.000 claims 2
231100000252 nontoxic Toxicity 0.000 claims 2
230000003000 nontoxic effect Effects 0.000 claims 2
125000006701 (C1-C7) alkyl group Chemical group 0.000 claims 1
WXVUCYGQHWWZCD-UHFFFAOYSA-N 4-amino-N-[1-(cyclopropylmethyl)-2-oxopyrimidin-4-yl]benzenesulfonamide Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=NC(=O)N(CC2CC2)C=C1 WXVUCYGQHWWZCD-UHFFFAOYSA-N 0.000 claims 1
LKSHWQPQADAFLK-UHFFFAOYSA-N 4-amino-n-(1-cyclopropyl-5-methyl-2-oxopyrimidin-4-yl)benzenesulfonamide Chemical compound O=C1N=C(NS(=O)(=O)C=2C=CC(N)=CC=2)C(C)=CN1C1CC1 LKSHWQPQADAFLK-UHFFFAOYSA-N 0.000 claims 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 70
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 66
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 43
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 42
238000002844 melting Methods 0.000 description 40
230000008018 melting Effects 0.000 description 40
239000000243 solution Substances 0.000 description 39
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 29
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 27
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 27
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 20
239000000047 product Substances 0.000 description 17
239000002244 precipitate Substances 0.000 description 16
238000006243 chemical reaction Methods 0.000 description 15
238000003756 stirring Methods 0.000 description 15
238000001816 cooling Methods 0.000 description 13
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 10
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 10
238000010992 reflux Methods 0.000 description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
229960000583 acetic acid Drugs 0.000 description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 7
238000002425 crystallisation Methods 0.000 description 7
230000008025 crystallization Effects 0.000 description 7
238000001953 recrystallisation Methods 0.000 description 7
238000009835 boiling Methods 0.000 description 6
229910021529 ammonia Inorganic materials 0.000 description 5
239000002904 solvent Substances 0.000 description 5
150000003456 sulfonamides Chemical class 0.000 description 5
DXFLKFBBEGOBFE-UHFFFAOYSA-N 4-amino-1-cyclopentylpyrimidin-2-one Chemical compound O=C1N=C(N)C=CN1C1CCCC1 DXFLKFBBEGOBFE-UHFFFAOYSA-N 0.000 description 4
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
229910052794 bromium Inorganic materials 0.000 description 4
239000012043 crude product Substances 0.000 description 4
238000001914 filtration Methods 0.000 description 4
238000010438 heat treatment Methods 0.000 description 4
GKKCIDNWFBPDBW-UHFFFAOYSA-M potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 description 4
238000011282 treatment Methods 0.000 description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000007864 aqueous solution Substances 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
MNQAFTPPCAKAHU-UHFFFAOYSA-N n-[4-[[1-(cyclopropylmethyl)-2-oxopyrimidin-4-yl]sulfamoyl]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1S(=O)(=O)NC1=NC(=O)N(CC2CC2)C=C1 MNQAFTPPCAKAHU-UHFFFAOYSA-N 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
238000007127 saponification reaction Methods 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
UJAAQJZEVGWFCM-UHFFFAOYSA-N 1-(2-cyanoethyl)-1-(cyclopropylmethyl)urea Chemical compound N#CCCN(C(=O)N)CC1CC1 UJAAQJZEVGWFCM-UHFFFAOYSA-N 0.000 description 2
IVACNLAJPODRBE-UHFFFAOYSA-N 1-(2-cyanoethyl)-1-cyclohexylurea Chemical compound N#CCCN(C(=O)N)C1CCCCC1 IVACNLAJPODRBE-UHFFFAOYSA-N 0.000 description 2
WZIDXHYJYCPRGU-UHFFFAOYSA-N 1-(2-cyanoethyl)-1-cyclopentylurea Chemical compound N#CCCN(C(=O)N)C1CCCC1 WZIDXHYJYCPRGU-UHFFFAOYSA-N 0.000 description 2
HMVIXXCBEDSDKF-UHFFFAOYSA-N 1-cyclohexyl-5-methyl-4-sulfanylidenepyrimidin-2-one Chemical compound O=C1NC(=S)C(C)=CN1C1CCCCC1 HMVIXXCBEDSDKF-UHFFFAOYSA-N 0.000 description 2
VDCSNZWCSQPFTQ-UHFFFAOYSA-N 1-cyclopropyl-5-methyl-4-sulfanylidenepyrimidin-2-one Chemical compound O=C1NC(=S)C(C)=CN1C1CC1 VDCSNZWCSQPFTQ-UHFFFAOYSA-N 0.000 description 2
SKGBDXKGMAITTB-UHFFFAOYSA-N 1-ethyl-5-methyl-4-sulfanylidenepyrimidin-2-one Chemical compound CCN1C=C(C)C(=S)NC1=O SKGBDXKGMAITTB-UHFFFAOYSA-N 0.000 description 2
OLUJYRYCQHJDKJ-UHFFFAOYSA-N 3-(cyclohexylamino)propanenitrile Chemical compound N#CCCNC1CCCCC1 OLUJYRYCQHJDKJ-UHFFFAOYSA-N 0.000 description 2
YHGZCPAPXDXHCY-UHFFFAOYSA-N 3-(cyclopentylamino)propanenitrile Chemical compound N#CCCNC1CCCC1 YHGZCPAPXDXHCY-UHFFFAOYSA-N 0.000 description 2
OZHWHTICSNFGBZ-UHFFFAOYSA-N 3-(cyclopropylamino)propanenitrile Chemical compound N#CCCNC1CC1 OZHWHTICSNFGBZ-UHFFFAOYSA-N 0.000 description 2
TXBNHIOKNSJQMO-UHFFFAOYSA-N 3-(cyclopropylmethylamino)propanenitrile Chemical compound N#CCCNCC1CC1 TXBNHIOKNSJQMO-UHFFFAOYSA-N 0.000 description 2
SDPKJYGDPREKJW-UHFFFAOYSA-N 4-amino-1-(cyclopropylmethyl)pyrimidin-2-one Chemical compound O=C1N=C(N)C=CN1CC1CC1 SDPKJYGDPREKJW-UHFFFAOYSA-N 0.000 description 2
VKDUGGUNZRZXNW-UHFFFAOYSA-N 4-amino-1-cyclohexyl-5-methylpyrimidin-2-one Chemical compound O=C1N=C(N)C(C)=CN1C1CCCCC1 VKDUGGUNZRZXNW-UHFFFAOYSA-N 0.000 description 2
TWZFIOJEBDZSAQ-UHFFFAOYSA-N 4-amino-1-cyclohexylpyrimidin-2-one Chemical compound O=C1N=C(N)C=CN1C1CCCCC1 TWZFIOJEBDZSAQ-UHFFFAOYSA-N 0.000 description 2
OBHLPOCPCDGLOD-UHFFFAOYSA-N 4-amino-1-cyclopropyl-5-methylpyrimidin-2-one Chemical compound O=C1N=C(N)C(C)=CN1C1CC1 OBHLPOCPCDGLOD-UHFFFAOYSA-N 0.000 description 2
GGBCQYHNNBOTGS-UHFFFAOYSA-N 4-amino-1-cyclopropylpyrimidin-2-one Chemical compound O=C1N=C(N)C=CN1C1CC1 GGBCQYHNNBOTGS-UHFFFAOYSA-N 0.000 description 2
RZSBPSHFIILPJP-UHFFFAOYSA-N 4-amino-1-ethyl-5-methylpyrimidin-2-one Chemical compound CCN1C=C(C)C(N)=NC1=O RZSBPSHFIILPJP-UHFFFAOYSA-N 0.000 description 2
HCRHTGNBOHNVDE-UHFFFAOYSA-N 6-amino-3-(cyclopropylmethyl)-4,5-dihydropyrimidin-2-one Chemical compound C1CC(N)=NC(=O)N1CC1CC1 HCRHTGNBOHNVDE-UHFFFAOYSA-N 0.000 description 2
DEFJDLZWCNNPCA-UHFFFAOYSA-N 6-amino-5-bromo-3-(cyclopropylmethyl)-4,5-dihydropyrimidin-2-one Chemical compound C1C(Br)C(N)=NC(=O)N1CC1CC1 DEFJDLZWCNNPCA-UHFFFAOYSA-N 0.000 description 2
QXEZOLKIGBXPJY-UHFFFAOYSA-N 6-amino-5-bromo-3-cyclohexyl-4,5-dihydropyrimidin-2-one Chemical compound C1C(Br)C(N)=NC(=O)N1C1CCCCC1 QXEZOLKIGBXPJY-UHFFFAOYSA-N 0.000 description 2
SSSDWZFUOHOUAC-UHFFFAOYSA-N 6-amino-5-bromo-3-cyclopentyl-4,5-dihydropyrimidin-2-one Chemical compound C1C(Br)C(N)=NC(=O)N1C1CCCC1 SSSDWZFUOHOUAC-UHFFFAOYSA-N 0.000 description 2
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 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
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
241000699670 Mus sp. Species 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
241000193996 Streptococcus pyogenes Species 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
239000004480 active ingredient Substances 0.000 description 2
125000004442 acylamino group Chemical group 0.000 description 2
150000008044 alkali metal hydroxides Chemical class 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
239000003242 anti bacterial agent Substances 0.000 description 2
230000031709 bromination Effects 0.000 description 2
238000005893 bromination reaction Methods 0.000 description 2
239000002775 capsule Substances 0.000 description 2
238000005660 chlorination reaction Methods 0.000 description 2
PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
208000015181 infectious disease Diseases 0.000 description 2
239000002054 inoculum Substances 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
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
WGLAQCOYPXHGLA-UHFFFAOYSA-N n-[4-[(1-cyclopropyl-2-oxopyrimidin-4-yl)sulfamoyl]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1S(=O)(=O)NC1=NC(=O)N(C2CC2)C=C1 WGLAQCOYPXHGLA-UHFFFAOYSA-N 0.000 description 2
IPCSVZSSVZVIGE-UHFFFAOYSA-N n-hexadecanoic acid Natural products CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
239000006228 supernatant Substances 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-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
YZWCDHNWHIGMKJ-UHFFFAOYSA-N 1-(2-cyanoethyl)-1-cyclopropylurea Chemical compound N#CCCN(C(=O)N)C1CC1 YZWCDHNWHIGMKJ-UHFFFAOYSA-N 0.000 description 1
KMKDOEBFMRRNPY-UHFFFAOYSA-N 1-cyclohexyl-5-methylpyrimidine-2,4-dione Chemical compound O=C1NC(=O)C(C)=CN1C1CCCCC1 KMKDOEBFMRRNPY-UHFFFAOYSA-N 0.000 description 1
BKDADTHKLXIORH-UHFFFAOYSA-N 1-ethyl-5-methylpyrimidine-2,4-dione Chemical compound CCN1C=C(C)C(=O)NC1=O BKDADTHKLXIORH-UHFFFAOYSA-N 0.000 description 1
LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
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 1
GDNZSTZBWQUUBN-UHFFFAOYSA-N 4-amino-1-cyclopentylpyrimidin-2-one;hydrochloride Chemical compound Cl.O=C1N=C(N)C=CN1C1CCCC1 GDNZSTZBWQUUBN-UHFFFAOYSA-N 0.000 description 1
MIIYJRWPGFSJQB-UHFFFAOYSA-N 4-amino-N-(1-cyclohexyl-2-oxopyrimidin-4-yl)benzenesulfonamide Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=NC(=O)N(C2CCCCC2)C=C1 MIIYJRWPGFSJQB-UHFFFAOYSA-N 0.000 description 1
UCTDKWUUWDERBZ-UHFFFAOYSA-N 4-amino-N-(1-ethyl-5-methyl-2-oxopyrimidin-4-yl)benzenesulfonamide Chemical compound O=C1N(CC)C=C(C)C(NS(=O)(=O)C=2C=CC(N)=CC=2)=N1 UCTDKWUUWDERBZ-UHFFFAOYSA-N 0.000 description 1
KEEYRKYKLYARHO-UHFFFAOYSA-N 5-[(4,5-dimethoxy-2-methylphenyl)methyl]pyrimidine-2,4-diamine Chemical compound C1=C(OC)C(OC)=CC(C)=C1CC1=CN=C(N)N=C1N KEEYRKYKLYARHO-UHFFFAOYSA-N 0.000 description 1
WFBZIFZFHLQCPP-UHFFFAOYSA-N 5-[(4-amino-3,5-dimethoxyphenyl)methyl]pyrimidine-2,4-diamine Chemical compound COC1=C(N)C(OC)=CC(CC=2C(=NC(N)=NC=2)N)=C1 WFBZIFZFHLQCPP-UHFFFAOYSA-N 0.000 description 1
XHPZVBGIPQQTQW-UHFFFAOYSA-N 5-benzylpyrimidine-2,4-diamine Chemical compound NC1=NC(N)=NC=C1CC1=CC=CC=C1 XHPZVBGIPQQTQW-UHFFFAOYSA-N 0.000 description 1
TZPBOSYHEYVHTI-UHFFFAOYSA-N 6-amino-5-bromo-3-cyclopropyl-4,5-dihydropyrimidin-2-one Chemical compound C1C(Br)C(N)=NC(=O)N1C1CC1 TZPBOSYHEYVHTI-UHFFFAOYSA-N 0.000 description 1
QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
244000215068 Acacia senegal Species 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
HTJDQJBWANPRPF-UHFFFAOYSA-N Cyclopropylamine Chemical compound NC1CC1 HTJDQJBWANPRPF-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
229920000084 Gum arabic Polymers 0.000 description 1
239000005642 Oleic acid Substances 0.000 description 1
ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
235000021314 Palmitic acid Nutrition 0.000 description 1
244000110797 Polygonum persicaria Species 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
239000000205 acacia gum Substances 0.000 description 1
235000010489 acacia gum Nutrition 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
238000006136 alcoholysis reaction Methods 0.000 description 1
150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
239000012670 alkaline solution Substances 0.000 description 1
125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
125000004414 alkyl thio group Chemical group 0.000 description 1
BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
239000000538 analytical sample Substances 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
125000004391 aryl sulfonyl group Chemical group 0.000 description 1
125000005279 aryl sulfonyloxy group Chemical group 0.000 description 1
238000011888 autopsy Methods 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
239000000872 buffer Substances 0.000 description 1
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
235000015165 citric acid Nutrition 0.000 description 1
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
NISGSNTVMOOSJQ-UHFFFAOYSA-N cyclopentanamine Chemical compound NC1CCCC1 NISGSNTVMOOSJQ-UHFFFAOYSA-N 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
IGSKHXTUVXSOMB-UHFFFAOYSA-N cyclopropylmethanamine Chemical compound NCC1CC1 IGSKHXTUVXSOMB-UHFFFAOYSA-N 0.000 description 1
230000020176 deacylation Effects 0.000 description 1
238000005947 deacylation reaction Methods 0.000 description 1
238000003745 diagnosis Methods 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000008298 dragée Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
QQZJNIROVDUCOK-UHFFFAOYSA-N ethyl n-(2-methyl-3-piperidin-1-ylprop-2-enethioyl)carbamate Chemical compound CCOC(=O)NC(=S)C(C)=CN1CCCCC1 QQZJNIROVDUCOK-UHFFFAOYSA-N 0.000 description 1
150000004665 fatty acids Chemical group 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
235000011087 fumaric acid Nutrition 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
235000011187 glycerol Nutrition 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
230000001524 infective effect Effects 0.000 description 1
QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
239000001630 malic acid Substances 0.000 description 1
235000011090 malic acid Nutrition 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
235000013336 milk Nutrition 0.000 description 1
239000008267 milk Substances 0.000 description 1
210000004080 milk Anatomy 0.000 description 1
231100000668 minimum lethal dose Toxicity 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
GPOPCPIQIAIAQP-UHFFFAOYSA-N n-[4-[(1-ethyl-5-methyl-2h-pyrimidin-4-yl)sulfamoyl]phenyl]acetamide Chemical compound CC1=CN(CC)CN=C1NS(=O)(=O)C1=CC=C(NC(C)=O)C=C1 GPOPCPIQIAIAQP-UHFFFAOYSA-N 0.000 description 1
125000005146 naphthylsulfonyl group Chemical group C1(=CC=CC2=CC=CC=C12)S(=O)(=O)* 0.000 description 1
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
229910052757 nitrogen Inorganic materials 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
239000002674 ointment Substances 0.000 description 1
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
230000003204 osmotic effect Effects 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
235000019271 petrolatum Nutrition 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
229920001515 polyalkylene glycol Polymers 0.000 description 1
239000002243 precursor Substances 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000000746 purification Methods 0.000 description 1
125000001453 quaternary ammonium group Chemical group 0.000 description 1
239000000523 sample Substances 0.000 description 1
CGRKCGWEOIQFRD-UHFFFAOYSA-N sodium;(4-aminophenyl)sulfonylazanide Chemical compound [Na+].NC1=CC=C(S([NH-])(=O)=O)C=C1 CGRKCGWEOIQFRD-UHFFFAOYSA-N 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008107 starch Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
210000002784 stomach Anatomy 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 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
239000002562 thickening agent Substances 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
230000007704 transition Effects 0.000 description 1
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical group CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
239000002023 wood Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/20—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D239/22—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/04—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms
- C07C275/18—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms of a saturated carbon skeleton containing rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/26—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of rings other than six-membered aromatic rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/56—One oxygen atom and one sulfur atom
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/69—Benzenesulfonamido-pyrimidines
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated

Landscapes

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

NO752174A 1974-06-19 1975-06-18 NO752174L (sk)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US480784A US3923792A (en)	1974-06-19	1974-06-19	Sulfacytosine derivatives

Publications (1)

Publication Number	Publication Date
NO752174L true NO752174L (sk)	1975-12-22

Family

ID=23909351

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO752174A NO752174L (sk)	1974-06-19	1975-06-18

Country Status (20)

Country	Link
US (1)	US3923792A (sk)
JP (1)	JPS5113781A (sk)
AU (1)	AU8222075A (sk)
BE (1)	BE830360A (sk)
DD (1)	DD118090A5 (sk)
DE (1)	DE2526795A1 (sk)
DK (1)	DK274575A (sk)
ES (1)	ES438661A1 (sk)
FI (1)	FI751786A (sk)
FR (1)	FR2275218A1 (sk)
GB (1)	GB1471399A (sk)
HU (1)	HU170013B (sk)
IE (1)	IE41563B1 (sk)
IL (1)	IL47500A0 (sk)
LU (1)	LU72748A1 (sk)
NL (1)	NL7507154A (sk)
NO (1)	NO752174L (sk)
PL (1)	PL95005B1 (sk)
SE (1)	SE7506907L (sk)
ZA (1)	ZA752558B (sk)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS54106635A (en) *	1978-01-30	1979-08-21	Mo Tekusuchiruni I	Apparatus for separating fiber and supplying said fiber into spinning chamber
US5153352A (en) *	1988-10-25	1992-10-06	Bristol-Myers Squibb Company	Process for preparation of intermediates of carbocyclic nucleoside analogs
IL92096A0 (en)	1988-10-25	1990-07-12	Abbott Lab	Carboxylic nucleoside analogs
US5246931A (en) *	1988-10-25	1993-09-21	Bristol-Myers Squibb Company	Carbocyclic nucleoside analogs
US4988703A (en) *	1989-05-22	1991-01-29	Abbott Laboratories	Carbocyclic nucleoside analogs with antiviral activity
EP0502690B1 (en) *	1991-03-05	1999-12-01	Ajinomoto Co., Inc.	Cyclopropane derivative
US7973060B2 (en) *	2005-10-13	2011-07-05	Crystalgenomics, Inc.	Fab I inhibitor and process for preparing same

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3422098A (en) *	1962-12-14	1969-01-14	Ciba Geigy Corp	Sulfanilamido-pyrimidines
US3457278A (en) *	1964-10-15	1969-07-22	Geigy Chem Corp	Cyclopropyl-4-sulfanilamido-pyrimidines
US3375247A (en) *	1965-08-02	1968-03-26	Parke Davis & Co	Heterocyclic compounds and methods for their production

1974
- 1974-06-19 US US480784A patent/US3923792A/en not_active Expired - Lifetime
1975
- 1975-04-21 ZA ZA00752558A patent/ZA752558B/xx unknown
- 1975-06-16 FI FI751786A patent/FI751786A/fi not_active Application Discontinuation
- 1975-06-16 DE DE19752526795 patent/DE2526795A1/de active Pending
- 1975-06-16 SE SE7506907A patent/SE7506907L/xx unknown
- 1975-06-16 NL NL7507154A patent/NL7507154A/xx unknown
- 1975-06-17 IL IL47500A patent/IL47500A0/xx unknown
- 1975-06-17 FR FR7518866A patent/FR2275218A1/fr not_active Withdrawn
- 1975-06-17 JP JP50072813A patent/JPS5113781A/ja active Pending
- 1975-06-17 DD DD186692A patent/DD118090A5/xx unknown
- 1975-06-17 LU LU72748A patent/LU72748A1/xx unknown
- 1975-06-18 BE BE157434A patent/BE830360A/xx unknown
- 1975-06-18 AU AU82220/75A patent/AU8222075A/en not_active Expired
- 1975-06-18 NO NO752174A patent/NO752174L/no unknown
- 1975-06-18 GB GB2594275A patent/GB1471399A/en not_active Expired
- 1975-06-18 HU HUHO1807A patent/HU170013B/hu unknown
- 1975-06-18 IE IE1365/75A patent/IE41563B1/en unknown
- 1975-06-18 DK DK274575A patent/DK274575A/da unknown
- 1975-06-18 ES ES438661A patent/ES438661A1/es not_active Expired
- 1975-06-18 PL PL1975181325A patent/PL95005B1/pl unknown

Also Published As

Publication number	Publication date
FR2275218A1 (fr)	1976-01-16
GB1471399A (en)	1977-04-27
LU72748A1 (sk)	1976-11-11
HU170013B (sk)	1977-03-28
ZA752558B (en)	1976-03-31
IE41563L (en)	1975-12-19
JPS5113781A (sk)	1976-02-03
US3923792A (en)	1975-12-02
DK274575A (da)	1975-12-20
DE2526795A1 (de)	1976-01-08
IL47500A0 (en)	1975-08-31
FI751786A (sk)	1975-12-20
BE830360A (fr)	1975-12-18
PL95005B1 (sk)	1977-09-30
IE41563B1 (en)	1980-01-30
NL7507154A (nl)	1975-12-23
DD118090A5 (sk)	1976-02-12
ES438661A1 (es)	1977-03-01
SE7506907L (sv)	1975-12-22
AU8222075A (en)	1976-12-23

Publication	Publication Date	Title
KR910006806B1 (ko)	1991-09-02	퀴놀린 유도체의 제조방법
EP0148725B1 (en)	1987-05-06	Sulfonamido-benzamide derivatives
NO156385B (no)	1987-06-01	Anordning for laasing av dreibare maskinelementer.
NO170883B (no)	1992-09-14	Fremgangsmaate for fremstilling av 2-amino-5-hydroksy-4-metylpyrimidin-derivater
NO173442B (no)	1993-09-06	Analogifremgangsmaate for fremstilling av terapeutisk aktive pyrimidin-derivater
EP0769007A1 (en)	1997-04-23	2-ureido-benzamide derivatives
US4774249A (en)	1988-09-27	Pyrimidine derivatives for treating malaria
CS241016B2 (en)	1986-03-13	Method of new n-(2-(or)pyrrolidinylmethyl)-benzamides production substituted in positions 2,3,4,5,6
NO863790L (no)	1987-03-25	Kinolinderivater.
NO752174L (sk)	1975-12-22
NO852133L (no)	1985-12-02	Analogifremgangsmaate for fremstilling av terapeutisk aktive pyrrolidinon-derivater.
SK14672001A3 (sk)	2002-11-06	Spôsob syntézy a kryštalizácie zlúčenín obsahujúcich piperazínový kruh
NO163597B (no)	1990-03-19	Styreinnretning for et ett-eller tosporet kjoeretoey.
KR20010024258A (ko)	2001-03-26	포스포리파제 저해제로 사용되는9,10-디히드로-9,10-에타노안트라센 유도체
DE2443682C2 (de)	1983-11-10	Neue 2,4-Diamino-5-benzylpyrimidine
FI73988C (fi)	1987-12-10	Foerfarande foer framstaellning av nya kardiotoniskt verkande pyridinyl-2-pyrimidinaminderivat.
RU2285001C2 (ru)	2006-10-10	Деслоратадин-полусульфат, способ его получения, фармацевтическая композиция, его содержащая, и способ получения исходного продукта
JPH05117273A (ja)	1993-05-14	医薬化合物
US6545149B2 (en)	2003-04-08	Synthesis and crystallization of piperazine ring-containing compounds
WO1988001270A1 (en)	1988-02-25	Pyridopyrimidinediones
US4016267A (en)	1977-04-05	Sulfacytosine derivatives
KR790001021B1 (ko)	1979-08-20	설폰아미드의 제조방법
US3433802A (en)	1969-03-18	3-(n-lower-alkylanilino)pyrrolidines
US3850927A (en)	1974-11-26	5-benzyl pyrimidines intermediates therefore,and method
NO327549B1 (no)	2009-08-10	Benzo[G]kinolinderivater for behandling av glaukom og myopi