NO763546L

NO763546L -

Info

Publication number: NO763546L
Authority: NO; Norway
Prior art keywords: acid; starting material; water; salts; sodium
Prior art date: 1971-01-20

Application number

NO763546A

Other languages

English (en)

Norwegian (no)

Inventor

A Furlenmeier

P Quitt

K Vogler

P Lanz

Original Assignee

Hoffmann La Roche

Priority date

1971-01-20

Filing date

1976-10-18

Publication date

1972-07-21

1971-01-20 Priority claimed from CH84871A external-priority patent/CH580631A5/xx

1972-07-21 Publication of NO763546L publication Critical patent/NO763546L/no

1976-10-18 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

1976-10-18 Priority to NO763546A priority Critical patent/NO763546L/no

Links

-1 ok so Chemical group 0.000 claims description 83
238000002360 preparation method Methods 0.000 claims description 32
150000001875 compounds Chemical class 0.000 claims description 24
150000003839 salts Chemical class 0.000 claims description 23
239000011734 sodium Substances 0.000 claims description 6
229910052708 sodium Inorganic materials 0.000 claims description 6
125000000217 alkyl group Chemical group 0.000 claims description 5
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims 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 claims description 4
125000003342 alkenyl group Chemical group 0.000 claims description 4
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
125000003373 pyrazinyl group Chemical group 0.000 claims description 4
125000002252 acyl group Chemical group 0.000 claims description 3
125000004432 carbon atom Chemical group C* 0.000 claims description 3
229940049954 penicillin Drugs 0.000 claims description 3
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
230000003115 biocidal effect Effects 0.000 claims description 2
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 2
229910052736 halogen Inorganic materials 0.000 claims description 2
125000001041 indolyl group Chemical group 0.000 claims description 2
125000004076 pyridyl group Chemical group 0.000 claims description 2
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 2
125000000168 pyrrolyl group Chemical group 0.000 claims description 2
125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 2
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
125000005843 halogen group Chemical group 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 111
239000007858 starting material Substances 0.000 description 80
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 59
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 57
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 55
239000000243 solution Substances 0.000 description 47
235000019439 ethyl acetate Nutrition 0.000 description 37
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 30
OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 29
239000002253 acid Substances 0.000 description 27
FCPVYOBCFFNJFS-LQDWTQKMSA-M benzylpenicillin sodium Chemical compound [Na+].N([C@H]1[C@H]2SC([C@@H](N2C1=O)C([O-])=O)(C)C)C(=O)CC1=CC=CC=C1 FCPVYOBCFFNJFS-LQDWTQKMSA-M 0.000 description 23
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 22
238000000354 decomposition reaction Methods 0.000 description 21
238000003756 stirring Methods 0.000 description 17
238000003776 cleavage reaction Methods 0.000 description 16
230000007017 scission Effects 0.000 description 16
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 14
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
NGHVIOIJCVXTGV-ALEPSDHESA-N 6-aminopenicillanic acid Chemical compound [O-]C(=O)[C@H]1C(C)(C)S[C@@H]2[C@H]([NH3+])C(=O)N21 NGHVIOIJCVXTGV-ALEPSDHESA-N 0.000 description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 12
NGHVIOIJCVXTGV-UHFFFAOYSA-N 6beta-amino-penicillanic acid Natural products OC(=O)C1C(C)(C)SC2C(N)C(=O)N21 NGHVIOIJCVXTGV-UHFFFAOYSA-N 0.000 description 11
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 11
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 11
238000004519 manufacturing process Methods 0.000 description 11
239000003921 oil Substances 0.000 description 11
235000019198 oils Nutrition 0.000 description 11
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 10
238000001035 drying Methods 0.000 description 10
239000011736 potassium bicarbonate Substances 0.000 description 10
229910000028 potassium bicarbonate Inorganic materials 0.000 description 10
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 10
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
239000003208 petroleum Substances 0.000 description 9
235000015497 potassium bicarbonate Nutrition 0.000 description 9
DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical group CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 9
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 8
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 8
239000000203 mixture Substances 0.000 description 8
238000005406 washing Methods 0.000 description 8
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
238000001704 evaporation Methods 0.000 description 7
230000008020 evaporation Effects 0.000 description 7
229910052943 magnesium sulfate Inorganic materials 0.000 description 7
235000019341 magnesium sulphate Nutrition 0.000 description 7
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
150000002148 esters Chemical class 0.000 description 6
239000000706 filtrate Substances 0.000 description 6
150000007513 acids Chemical class 0.000 description 5
239000003054 catalyst Substances 0.000 description 5
239000000284 extract Substances 0.000 description 5
239000011780 sodium chloride Substances 0.000 description 5
239000000126 substance Substances 0.000 description 5
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
229910052739 hydrogen Inorganic materials 0.000 description 4
239000001257 hydrogen Substances 0.000 description 4
125000006239 protecting group Chemical group 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
229910052938 sodium sulfate Inorganic materials 0.000 description 4
235000011152 sodium sulphate Nutrition 0.000 description 4
239000002904 solvent Substances 0.000 description 4
OSBDCZOPWJXASO-SNVBAGLBSA-N (2r)-4-methyl-2-(pyridine-3-carbonyloxy)pentanoic acid Chemical compound CC(C)C[C@H](C(O)=O)OC(=O)C1=CC=CN=C1 OSBDCZOPWJXASO-SNVBAGLBSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
229930182555 Penicillin Natural products 0.000 description 3
150000008064 anhydrides Chemical class 0.000 description 3
LNYCLASVFGVAII-GFCCVEGCSA-N benzyl (2r)-2-hydroxy-4-methylpentanoate Chemical compound CC(C)C[C@@H](O)C(=O)OCC1=CC=CC=C1 LNYCLASVFGVAII-GFCCVEGCSA-N 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
238000009835 boiling Methods 0.000 description 3
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 description 3
239000005457 ice water Substances 0.000 description 3
238000000034 method Methods 0.000 description 3
239000011591 potassium Substances 0.000 description 3
229910052700 potassium Inorganic materials 0.000 description 3
235000017557 sodium bicarbonate Nutrition 0.000 description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
VYPDUQYOLCLEGS-UHFFFAOYSA-M sodium;2-ethylhexanoate Chemical compound [Na+].CCCCC(CC)C([O-])=O VYPDUQYOLCLEGS-UHFFFAOYSA-M 0.000 description 3
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
JJIIJBVSYHWBIT-MRVPVSSYSA-N (2r)-2-(5-bromofuran-2-carbonyl)oxy-4-methylpentanoic acid Chemical compound CC(C)C[C@H](C(O)=O)OC(=O)C1=CC=C(Br)O1 JJIIJBVSYHWBIT-MRVPVSSYSA-N 0.000 description 2
AJVAZBQHVSBCBG-CQSZACIVSA-N (2r)-2-(7-chloroquinoline-4-carbonyl)oxy-4-methylpentanoic acid Chemical compound ClC1=CC=C2C(C(=O)O[C@H](CC(C)C)C(O)=O)=CC=NC2=C1 AJVAZBQHVSBCBG-CQSZACIVSA-N 0.000 description 2
MKNISDJDYYUMBA-LLVKDONJSA-N (2r)-2-[5-(methoxymethyl)furan-2-carbonyl]oxy-4-methylpentanoic acid Chemical compound COCC1=CC=C(C(=O)O[C@H](CC(C)C)C(O)=O)O1 MKNISDJDYYUMBA-LLVKDONJSA-N 0.000 description 2
UIGMHTGIJAVDDB-MRVPVSSYSA-N (2r)-4-methyl-2-(1,2-oxazole-3-carbonyloxy)pentanoic acid Chemical compound CC(C)C[C@H](C(O)=O)OC(=O)C=1C=CON=1 UIGMHTGIJAVDDB-MRVPVSSYSA-N 0.000 description 2
ZLGVTTNXFUCVGH-MRVPVSSYSA-N (2r)-4-methyl-2-(1,3-oxazole-4-carbonyloxy)pentanoic acid Chemical compound CC(C)C[C@H](C(O)=O)OC(=O)C1=COC=N1 ZLGVTTNXFUCVGH-MRVPVSSYSA-N 0.000 description 2
NEDVPRVZCTXJIH-SECBINFHSA-N (2r)-4-methyl-2-(1-methylimidazole-4-carbonyl)oxypentanoic acid Chemical compound CC(C)C[C@H](C(O)=O)OC(=O)C1=CN(C)C=N1 NEDVPRVZCTXJIH-SECBINFHSA-N 0.000 description 2
SQEGGWYFZFLOLL-SNVBAGLBSA-N (2r)-4-methyl-2-(5-methylfuran-2-carbonyl)oxypentanoic acid Chemical compound CC(C)C[C@H](C(O)=O)OC(=O)C1=CC=C(C)O1 SQEGGWYFZFLOLL-SNVBAGLBSA-N 0.000 description 2
GDGNUCAOGKIUOX-SNVBAGLBSA-N (2r)-4-methyl-2-(pyridine-4-carbonyloxy)pentanoic acid Chemical compound CC(C)C[C@H](C(O)=O)OC(=O)C1=CC=NC=C1 GDGNUCAOGKIUOX-SNVBAGLBSA-N 0.000 description 2
ZFVQSHMGJCZJHI-CQSZACIVSA-N (2r)-4-methyl-2-(quinoline-2-carbonyloxy)pentanoic acid Chemical compound C1=CC=CC2=NC(C(=O)O[C@H](CC(C)C)C(O)=O)=CC=C21 ZFVQSHMGJCZJHI-CQSZACIVSA-N 0.000 description 2
ARBSULDLPGESAS-CQSZACIVSA-N (2r)-4-methyl-2-(quinoline-4-carbonyloxy)pentanoic acid Chemical compound C1=CC=C2C(C(=O)O[C@H](CC(C)C)C(O)=O)=CC=NC2=C1 ARBSULDLPGESAS-CQSZACIVSA-N 0.000 description 2
SSLARYBQMAXWKL-VIFPVBQESA-N (2s)-2-(furan-2-carbonyloxy)-4-methylpentanoic acid Chemical compound CC(C)C[C@@H](C(O)=O)OC(=O)C1=CC=CO1 SSLARYBQMAXWKL-VIFPVBQESA-N 0.000 description 2
OHSLCKWYVFUXIW-UHFFFAOYSA-N (4-methyl-1-oxo-1-phenylmethoxypentan-2-yl) pyridine-4-carboxylate Chemical compound C=1C=CC=CC=1COC(=O)C(CC(C)C)OC(=O)C1=CC=NC=C1 OHSLCKWYVFUXIW-UHFFFAOYSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
BSEHCAXAIKBAQF-UHFFFAOYSA-N 2-(pyridine-4-carbonyloxy)pentanoic acid Chemical compound CCCC(C(O)=O)OC(=O)C1=CC=NC=C1 BSEHCAXAIKBAQF-UHFFFAOYSA-N 0.000 description 2
SMNDYUVBFMFKNZ-UHFFFAOYSA-N 2-furoic acid Chemical compound OC(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-N 0.000 description 2
YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical compound N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-UHFFFAOYSA-N 0.000 description 2
GDGNUCAOGKIUOX-UHFFFAOYSA-N 4-methyl-2-(pyridine-4-carbonyloxy)pentanoic acid Chemical compound CC(C)CC(C(O)=O)OC(=O)C1=CC=NC=C1 GDGNUCAOGKIUOX-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
108010010803 Gelatin Proteins 0.000 description 2
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound 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
JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 2
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
WEKSWPWYOSZOCB-MRXNPFEDSA-N [(2r)-4-methyl-1-oxo-1-phenylmethoxypentan-2-yl] furan-2-carboxylate Chemical compound O([C@H](CC(C)C)C(=O)OCC=1C=CC=CC=1)C(=O)C1=CC=CO1 WEKSWPWYOSZOCB-MRXNPFEDSA-N 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
239000003708 ampul Substances 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
150000001540 azides Chemical class 0.000 description 2
239000002585 base Substances 0.000 description 2
IYMAUEAFOBSGCY-UHFFFAOYSA-N benzene;sulfurochloridic acid Chemical compound OS(Cl)(=O)=O.C1=CC=CC=C1 IYMAUEAFOBSGCY-UHFFFAOYSA-N 0.000 description 2
KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 2
229940073608 benzyl chloride Drugs 0.000 description 2
239000002775 capsule Substances 0.000 description 2
150000001718 carbodiimides Chemical class 0.000 description 2
238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
125000004185 ester group Chemical group 0.000 description 2
239000008273 gelatin Substances 0.000 description 2
229920000159 gelatin Polymers 0.000 description 2
235000019322 gelatine Nutrition 0.000 description 2
235000011852 gelatine desserts Nutrition 0.000 description 2
150000004820 halides Chemical class 0.000 description 2
150000002367 halogens Chemical group 0.000 description 2
TWBYWOBDOCUKOW-UHFFFAOYSA-N isonicotinic acid Chemical compound OC(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-N 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 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
229910000510 noble metal Inorganic materials 0.000 description 2
150000007530 organic bases Chemical class 0.000 description 2
229910052763 palladium Inorganic materials 0.000 description 2
239000000825 pharmaceutical preparation Substances 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
238000010992 reflux Methods 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000007921 spray Substances 0.000 description 2
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
OFEMXQVRZIAUCU-SNVBAGLBSA-N (2r)-2-(1,5-dimethylpyrazole-3-carbonyl)oxy-4-methylpentanoic acid Chemical compound CC(C)C[C@H](C(O)=O)OC(=O)C=1C=C(C)N(C)N=1 OFEMXQVRZIAUCU-SNVBAGLBSA-N 0.000 description 1
VVPWFARZBKNXDJ-GFCCVEGCSA-N (2r)-2-(1-benzofuran-2-carbonyloxy)-4-methylpentanoic acid Chemical compound C1=CC=C2OC(C(=O)O[C@H](CC(C)C)C(O)=O)=CC2=C1 VVPWFARZBKNXDJ-GFCCVEGCSA-N 0.000 description 1
TVSULVYVZMXTLT-LLVKDONJSA-N (2r)-2-(2,4-dimethylpyrimidine-5-carbonyl)oxy-4-methylpentanoic acid Chemical compound CC(C)C[C@H](C(O)=O)OC(=O)C1=CN=C(C)N=C1C TVSULVYVZMXTLT-LLVKDONJSA-N 0.000 description 1
UIORBEHBPDGKCX-MRVPVSSYSA-N (2r)-2-(2,6-dichloropyridine-4-carbonyl)oxy-4-methylpentanoic acid Chemical compound CC(C)C[C@H](C(O)=O)OC(=O)C1=CC(Cl)=NC(Cl)=C1 UIORBEHBPDGKCX-MRVPVSSYSA-N 0.000 description 1
VCUNADSEBUJGEK-SNVBAGLBSA-N (2r)-2-(2,6-dimethoxypyridine-4-carbonyl)oxy-4-methylpentanoic acid Chemical compound COC1=CC(C(=O)O[C@H](CC(C)C)C(O)=O)=CC(OC)=N1 VCUNADSEBUJGEK-SNVBAGLBSA-N 0.000 description 1
DVAZFJWFZDJEKV-SECBINFHSA-N (2r)-2-(2-acetamido-1,3-thiazole-4-carbonyl)oxy-4-methylpentanoic acid Chemical compound CC(C)C[C@H](C(O)=O)OC(=O)C1=CSC(NC(C)=O)=N1 DVAZFJWFZDJEKV-SECBINFHSA-N 0.000 description 1
QSBGAOFIIRPBOD-SECBINFHSA-N (2r)-2-(2-chloropyridine-3-carbonyl)oxy-4-methylpentanoic acid Chemical compound CC(C)C[C@H](C(O)=O)OC(=O)C1=CC=CN=C1Cl QSBGAOFIIRPBOD-SECBINFHSA-N 0.000 description 1
VAWVUZYZBLLQBV-SNVBAGLBSA-N (2r)-2-(2-methoxycarbonylpyridine-3-carbonyl)oxy-4-methylpentanoic acid Chemical compound COC(=O)C1=NC=CC=C1C(=O)O[C@H](CC(C)C)C(O)=O VAWVUZYZBLLQBV-SNVBAGLBSA-N 0.000 description 1
KCGZTYNLUUUYSQ-SNVBAGLBSA-N (2r)-2-(4-chloropyridine-2-carbonyl)oxy-4-methylpentanoic acid Chemical compound CC(C)C[C@H](C(O)=O)OC(=O)C1=CC(Cl)=CC=N1 KCGZTYNLUUUYSQ-SNVBAGLBSA-N 0.000 description 1
SSLARYBQMAXWKL-SECBINFHSA-N (2r)-2-(furan-2-carbonyloxy)-4-methylpentanoic acid Chemical compound CC(C)C[C@H](C(O)=O)OC(=O)C1=CC=CO1 SSLARYBQMAXWKL-SECBINFHSA-N 0.000 description 1
WATPKCFQXIEODK-MRVPVSSYSA-N (2r)-4-methyl-2-(3-methyl-1,2-oxazole-5-carbonyl)oxypentanoic acid Chemical compound CC(C)C[C@H](C(O)=O)OC(=O)C1=CC(C)=NO1 WATPKCFQXIEODK-MRVPVSSYSA-N 0.000 description 1
VKMXNHYCCDFQOC-SNVBAGLBSA-N (2r)-4-methyl-2-(oxane-4-carbonyloxy)pentanoic acid Chemical compound CC(C)C[C@H](C(O)=O)OC(=O)C1CCOCC1 VKMXNHYCCDFQOC-SNVBAGLBSA-N 0.000 description 1
CNQZUDHBDVRKPU-SECBINFHSA-N (2r)-4-methyl-2-(pyrazine-2-carbonyloxy)pentanoic acid Chemical compound CC(C)C[C@H](C(O)=O)OC(=O)C1=CN=CC=N1 CNQZUDHBDVRKPU-SECBINFHSA-N 0.000 description 1
PEAYGOHZSXFHLA-SECBINFHSA-N (2r)-4-methyl-2-(pyrimidine-5-carbonyloxy)pentanoic acid Chemical compound CC(C)C[C@H](C(O)=O)OC(=O)C1=CN=CN=C1 PEAYGOHZSXFHLA-SECBINFHSA-N 0.000 description 1
REOZFDLKPATYPR-SSDOTTSWSA-N (2r)-4-methyl-2-(thiadiazole-4-carbonyloxy)pentanoic acid Chemical compound CC(C)C[C@H](C(O)=O)OC(=O)C1=CSN=N1 REOZFDLKPATYPR-SSDOTTSWSA-N 0.000 description 1
OVFCLPREBSLKBC-MRVPVSSYSA-N (2r)-4-methyl-2-(thiophene-2-carbonyloxy)pentanoic acid Chemical compound CC(C)C[C@H](C(O)=O)OC(=O)C1=CC=CS1 OVFCLPREBSLKBC-MRVPVSSYSA-N 0.000 description 1
GDGNUCAOGKIUOX-JTQLQIEISA-N (2s)-4-methyl-2-(pyridine-4-carbonyloxy)pentanoic acid Chemical compound CC(C)C[C@@H](C(O)=O)OC(=O)C1=CC=NC=C1 GDGNUCAOGKIUOX-JTQLQIEISA-N 0.000 description 1
KIPJXTNNWKIVJE-PPHPATTJSA-N (2s)-4-methyl-2-(pyridine-4-carbonyloxy)pentanoic acid;hydrochloride Chemical compound Cl.CC(C)C[C@@H](C(O)=O)OC(=O)C1=CC=NC=C1 KIPJXTNNWKIVJE-PPHPATTJSA-N 0.000 description 1
125000006274 (C1-C3)alkoxy group Chemical group 0.000 description 1
NGEWQZIDQIYUNV-SCSAIBSYSA-N (R)-2-hydroxy-3-methylbutyric acid Chemical compound CC(C)[C@@H](O)C(O)=O NGEWQZIDQIYUNV-SCSAIBSYSA-N 0.000 description 1
LVRFTAZAXQPQHI-RXMQYKEDSA-N (R)-2-hydroxy-4-methylpentanoic acid Chemical compound CC(C)C[C@@H](O)C(O)=O LVRFTAZAXQPQHI-RXMQYKEDSA-N 0.000 description 1
SYTBZMRGLBWNTM-SNVBAGLBSA-N (R)-flurbiprofen Chemical compound FC1=CC([C@H](C(O)=O)C)=CC=C1C1=CC=CC=C1 SYTBZMRGLBWNTM-SNVBAGLBSA-N 0.000 description 1
125000004512 1,2,3-thiadiazol-4-yl group Chemical group S1N=NC(=C1)* 0.000 description 1
125000004511 1,2,3-thiadiazolyl group Chemical group 0.000 description 1
PXRXGHUTKHXUGF-UHFFFAOYSA-N 1,5-dimethylpyrazole-3-carboxylic acid Chemical compound CC1=CC(C(O)=O)=NN1C PXRXGHUTKHXUGF-UHFFFAOYSA-N 0.000 description 1
OHVLMTFVQDZYHP-UHFFFAOYSA-N 1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-2-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound N1N=NC=2CN(CCC=21)C(CN1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)=O OHVLMTFVQDZYHP-UHFFFAOYSA-N 0.000 description 1
JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 description 1
LDXJRKWFNNFDSA-UHFFFAOYSA-N 2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound C1CN(CC2=NNN=C21)CC(=O)N3CCN(CC3)C4=CN=C(N=C4)NCC5=CC(=CC=C5)OC(F)(F)F LDXJRKWFNNFDSA-UHFFFAOYSA-N 0.000 description 1
HYRBOSOPQAAOQR-UHFFFAOYSA-N 2-(2,6-dimethylpyridine-4-carbonyl)oxy-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)OC(=O)C1=CC(C)=NC(C)=C1 HYRBOSOPQAAOQR-UHFFFAOYSA-N 0.000 description 1
MLLFLUIKXQWNAT-UHFFFAOYSA-N 2-(furan-2-carbonyloxy)pentanoic acid Chemical compound CCCC(C(O)=O)OC(=O)C1=CC=CO1 MLLFLUIKXQWNAT-UHFFFAOYSA-N 0.000 description 1
UTWXJAARHQBFNZ-UHFFFAOYSA-N 2-(furan-3-carbonyloxy)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)OC(=O)C=1C=COC=1 UTWXJAARHQBFNZ-UHFFFAOYSA-N 0.000 description 1
IHCCLXNEEPMSIO-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperidin-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1CCN(CC1)CC(=O)N1CC2=C(CC1)NN=N2 IHCCLXNEEPMSIO-UHFFFAOYSA-N 0.000 description 1
ZKINQVZUSLLCJY-UHFFFAOYSA-N 2-acetamido-1,3-thiazole-4-carboxylic acid Chemical compound CC(=O)NC1=NC(C(O)=O)=CS1 ZKINQVZUSLLCJY-UHFFFAOYSA-N 0.000 description 1
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
JKHMZLLAKFDHRK-UHFFFAOYSA-N 4-methyl-2-(1h-pyrrole-2-carbonyloxy)pentanoic acid Chemical compound CC(C)CC(C(O)=O)OC(=O)C1=CC=CN1 JKHMZLLAKFDHRK-UHFFFAOYSA-N 0.000 description 1
HLEGKILRVNZIFW-UHFFFAOYSA-N 4-methylbenzenesulfonic acid;(4-methyl-1-oxo-1-phenylmethoxypentan-2-yl) pyridine-4-carboxylate Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1.C=1C=CC=CC=1COC(=O)C(CC(C)C)OC(=O)C1=CC=NC=C1 HLEGKILRVNZIFW-UHFFFAOYSA-N 0.000 description 1
ODHCTXKNWHHXJC-VKHMYHEASA-N 5-oxo-L-proline Chemical compound OC(=O)[C@@H]1CCC(=O)N1 ODHCTXKNWHHXJC-VKHMYHEASA-N 0.000 description 1
DEXFNLNNUZKHNO-UHFFFAOYSA-N 6-[3-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperidin-1-yl]-3-oxopropyl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1CCN(CC1)C(CCC1=CC2=C(NC(O2)=O)C=C1)=O DEXFNLNNUZKHNO-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
BWLUMTFWVZZZND-UHFFFAOYSA-N Dibenzylamine Chemical compound C=1C=CC=CC=1CNCC1=CC=CC=C1 BWLUMTFWVZZZND-UHFFFAOYSA-N 0.000 description 1
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
241001529251 Gallinago gallinago Species 0.000 description 1
229920000084 Gum arabic Polymers 0.000 description 1
NGEWQZIDQIYUNV-UHFFFAOYSA-N L-valinic acid Natural products CC(C)C(O)C(O)=O NGEWQZIDQIYUNV-UHFFFAOYSA-N 0.000 description 1
HTLZVHNRZJPSMI-UHFFFAOYSA-N N-ethylpiperidine Chemical compound CCN1CCCCC1 HTLZVHNRZJPSMI-UHFFFAOYSA-N 0.000 description 1
150000001204 N-oxides Chemical class 0.000 description 1
ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical class C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
241000978776 Senegalia senegal Species 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
241001441724 Tetraodontidae Species 0.000 description 1
NQPDZGIKBAWPEJ-UHFFFAOYSA-N Valeric acid Natural products CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
QOMGYJMLZYLHOT-SECBINFHSA-N [(2r)-1-chloro-4-methyl-1-oxopentan-2-yl] furan-2-carboxylate Chemical compound CC(C)C[C@H](C(Cl)=O)OC(=O)C1=CC=CO1 QOMGYJMLZYLHOT-SECBINFHSA-N 0.000 description 1
PPMITUBLXLBABT-HNCPQSOCSA-N [(2r)-1-chloro-4-methyl-1-oxopentan-2-yl] pyridine-4-carboxylate;hydrochloride Chemical compound Cl.CC(C)C[C@H](C(Cl)=O)OC(=O)C1=CC=NC=C1 PPMITUBLXLBABT-HNCPQSOCSA-N 0.000 description 1
FHKPLLOSJHHKNU-INIZCTEOSA-N [(3S)-3-[8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]-(oxan-4-yl)methanone Chemical compound C(C)N1N=CC(=C1C)C=1N(C2=NC=NC(=C2N=1)O[C@@H]1CN(CC1)C(=O)C1CCOCC1)C FHKPLLOSJHHKNU-INIZCTEOSA-N 0.000 description 1
239000000205 acacia gum Substances 0.000 description 1
235000010489 acacia gum Nutrition 0.000 description 1
229960000583 acetic acid Drugs 0.000 description 1
ODHCTXKNWHHXJC-UHFFFAOYSA-N acide pyroglutamique Natural products OC(=O)C1CCC(=O)N1 ODHCTXKNWHHXJC-UHFFFAOYSA-N 0.000 description 1
239000003929 acidic solution Substances 0.000 description 1
239000013543 active substance Substances 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
FGKJLKRYENPLQH-UHFFFAOYSA-N alpha-isocaproic acid Natural products CC(C)CCC(O)=O FGKJLKRYENPLQH-UHFFFAOYSA-N 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
230000000845 anti-microbial effect Effects 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 1
CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 1
XANDRLFOMIFEFY-LLVKDONJSA-N benzyl (2r)-2-hydroxy-3-methylbutanoate Chemical compound CC(C)[C@@H](O)C(=O)OCC1=CC=CC=C1 XANDRLFOMIFEFY-LLVKDONJSA-N 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
150000001649 bromium compounds Chemical class 0.000 description 1
239000000872 buffer Substances 0.000 description 1
125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
239000001110 calcium chloride Substances 0.000 description 1
229910001628 calcium chloride Inorganic materials 0.000 description 1
159000000007 calcium salts Chemical class 0.000 description 1
239000012876 carrier material Substances 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
239000003245 coal Substances 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
IQFVPQOLBLOTPF-HKXUKFGYSA-L congo red Chemical compound [Na+].[Na+].C1=CC=CC2=C(N)C(/N=N/C3=CC=C(C=C3)C3=CC=C(C=C3)/N=N/C3=C(C4=CC=CC=C4C(=C3)S([O-])(=O)=O)N)=CC(S([O-])(=O)=O)=C21 IQFVPQOLBLOTPF-HKXUKFGYSA-L 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
229920006038 crystalline resin Polymers 0.000 description 1
125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 description 1
238000010908 decantation Methods 0.000 description 1
239000000645 desinfectant Substances 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
239000008298 dragée Substances 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
239000002024 ethyl acetate extract Substances 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
238000000605 extraction Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
150000002222 fluorine compounds Chemical class 0.000 description 1
125000002541 furyl group Chemical group 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
150000004677 hydrates Chemical class 0.000 description 1
230000036571 hydration Effects 0.000 description 1
238000006703 hydration reaction Methods 0.000 description 1
150000007928 imidazolide derivatives Chemical class 0.000 description 1
125000002883 imidazolyl group Chemical group 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
125000005956 isoquinolyl group Chemical group 0.000 description 1
125000000842 isoxazolyl group Chemical group 0.000 description 1
239000007788 liquid Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
239000000155 melt Substances 0.000 description 1
125000005394 methallyl group Chemical group 0.000 description 1
244000005700 microbiome Species 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000011707 mineral Substances 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 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
235000015097 nutrients Nutrition 0.000 description 1
239000002674 ointment Substances 0.000 description 1
230000003204 osmotic effect Effects 0.000 description 1
125000002971 oxazolyl group Chemical group 0.000 description 1
125000004043 oxo group Chemical group O=* 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
150000002960 penicillins Chemical class 0.000 description 1
125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
235000019271 petrolatum Nutrition 0.000 description 1
239000012071 phase Substances 0.000 description 1
NMHMNPHRMNGLLB-UHFFFAOYSA-N phloretic acid Chemical compound OC(=O)CCC1=CC=C(O)C=C1 NMHMNPHRMNGLLB-UHFFFAOYSA-N 0.000 description 1
229920001515 polyalkylene glycol Polymers 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
235000011181 potassium carbonates Nutrition 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
229960004919 procaine Drugs 0.000 description 1
108090000765 processed proteins & peptides Proteins 0.000 description 1
239000000047 product Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
125000003226 pyrazolyl group Chemical group 0.000 description 1
125000000714 pyrimidinyl group Chemical group 0.000 description 1
125000005493 quinolyl group Chemical group 0.000 description 1
229920005989 resin Polymers 0.000 description 1
239000011347 resin Substances 0.000 description 1
125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
238000005507 spraying Methods 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
210000002784 stomach Anatomy 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
239000000725 suspension 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
JXHBSPWXNWZNDR-MRVPVSSYSA-N tert-butyl (2r)-2-hydroxy-4-methylpentanoate Chemical compound CC(C)C[C@@H](O)C(=O)OC(C)(C)C JXHBSPWXNWZNDR-MRVPVSSYSA-N 0.000 description 1
FQFILJKFZCVHNH-UHFFFAOYSA-N tert-butyl n-[3-[(5-bromo-2-chloropyrimidin-4-yl)amino]propyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCCNC1=NC(Cl)=NC=C1Br FQFILJKFZCVHNH-UHFFFAOYSA-N 0.000 description 1
125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
HJZYBDPHAHGHAZ-UHFFFAOYSA-N thiadiazole-4-carboxylic acid Chemical compound OC(=O)C1=CSN=N1 HJZYBDPHAHGHAZ-UHFFFAOYSA-N 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
125000005208 trialkylammonium group Chemical group 0.000 description 1
NRTLTGGGUQIRRT-UHFFFAOYSA-N triethylazanium;bromide Chemical compound [Br-].CC[NH+](CC)CC NRTLTGGGUQIRRT-UHFFFAOYSA-N 0.000 description 1
ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
229940005605 valeric acid Drugs 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
238000009736 wetting Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
239000002023 wood Substances 0.000 description 1

NO763546A 1971-01-20 1976-10-18 NO763546L (fr)