IL97476A

IL97476A - History of N-phenylglycinamide, their preparation, pharmaceutical preparations containing them and their application

History of N-phenylglycinamide, their preparation, pharmaceutical preparations containing them and their application

Info

Publication number: IL97476A
Authority: IL; Israel
Prior art keywords: tert; radical; butyl; acetate; acetamido
Prior art date: 1990-03-07

Application number

IL9747691A

Other languages

English (en)

Hebrew (he)

Other versions

IL97476A0 (en

Original Assignee

Rhone Poulenc Rorer Sa

Priority date

1990-03-07

Filing date

1991-03-07

Publication date

1996-07-23

1990-03-07 Priority claimed from FR9002889A external-priority patent/FR2659334B1/fr

1991-03-07 Application filed by Rhone Poulenc Rorer Sa filed Critical Rhone Poulenc Rorer Sa

1992-06-21 Publication of IL97476A0 publication Critical patent/IL97476A0/xx

1996-07-23 Publication of IL97476A publication Critical patent/IL97476A/en

Links

238000002360 preparation method Methods 0.000 title claims abstract description 105
QRKJNCRCYBKANP-UHFFFAOYSA-N 2-amino-n-phenylacetamide Chemical class NCC(=O)NC1=CC=CC=C1 QRKJNCRCYBKANP-UHFFFAOYSA-N 0.000 title claims description 17
239000008194 pharmaceutical composition Substances 0.000 title claims description 7
125000000217 alkyl group Chemical group 0.000 claims abstract description 36
150000001875 compounds Chemical class 0.000 claims abstract description 33
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 32
125000003545 alkoxy group Chemical group 0.000 claims abstract description 30
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims abstract description 25
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 12
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 11
125000005112 cycloalkylalkoxy group Chemical group 0.000 claims abstract description 6
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 5
125000001041 indolyl group Chemical class 0.000 claims abstract description 5
125000001624 naphthyl group Chemical class 0.000 claims abstract description 5
125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 5
125000001316 cycloalkyl alkyl group Chemical group 0.000 claims abstract description 3
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 3
125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims abstract description 3
-1 alkoxycarbonyl radical Chemical class 0.000 claims description 192
238000000034 method Methods 0.000 claims description 71
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 67
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 53
125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 39
239000002253 acid Substances 0.000 claims description 27
125000005843 halogen group Chemical group 0.000 claims description 23
125000001424 substituent group Chemical group 0.000 claims description 23
150000003254 radicals Chemical class 0.000 claims description 22
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 21
WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 18
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 17
125000004414 alkyl thio group Chemical group 0.000 claims description 16
150000001412 amines Chemical class 0.000 claims description 16
125000004432 carbon atom Chemical group C* 0.000 claims description 12
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 10
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
239000005711 Benzoic acid Substances 0.000 claims description 9
125000002252 acyl group Chemical group 0.000 claims description 9
235000010233 benzoic acid Nutrition 0.000 claims description 9
239000012948 isocyanate Substances 0.000 claims description 8
150000002513 isocyanates Chemical class 0.000 claims description 8
150000002148 esters Chemical class 0.000 claims description 7
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
229960003424 phenylacetic acid Drugs 0.000 claims description 7
239000003279 phenylacetic acid Substances 0.000 claims description 7
229920006395 saturated elastomer Polymers 0.000 claims description 7
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 6
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 6
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
239000003795 chemical substances by application Substances 0.000 claims description 5
230000002265 prevention Effects 0.000 claims description 5
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
102100021022 Gastrin Human genes 0.000 claims description 4
108010052343 Gastrins Proteins 0.000 claims description 4
125000004694 alkoxyaminocarbonyl group Chemical group 0.000 claims description 4
125000004666 alkoxyiminoalkyl group Chemical group 0.000 claims description 4
125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 4
125000002947 alkylene group Chemical group 0.000 claims description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
229910052794 bromium Inorganic materials 0.000 claims description 4
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
229910052799 carbon Inorganic materials 0.000 claims description 4
AOXOCDRNSPFDPE-UKEONUMOSA-N chembl413654 Chemical compound C([C@H](C(=O)NCC(=O)N[C@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@H](CCSC)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC=1C=CC=CC=1)C(N)=O)NC(=O)[C@@H](C)NC(=O)[C@@H](CCC(O)=O)NC(=O)[C@@H](CCC(O)=O)NC(=O)[C@@H](CCC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H]1N(CCC1)C(=O)CNC(=O)[C@@H](N)CCC(O)=O)C1=CC=C(O)C=C1 AOXOCDRNSPFDPE-UKEONUMOSA-N 0.000 claims description 4
239000000460 chlorine Substances 0.000 claims description 4
229910052801 chlorine Inorganic materials 0.000 claims description 4
125000000000 cycloalkoxy group Chemical group 0.000 claims description 4
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 4
210000005095 gastrointestinal system Anatomy 0.000 claims description 4
210000000653 nervous system Anatomy 0.000 claims description 4
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 3
TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical compound [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 claims description 3
229910052760 oxygen Inorganic materials 0.000 claims description 3
125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
125000004442 acylamino group Chemical group 0.000 claims description 2
125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
125000004429 atom Chemical group 0.000 claims description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
125000004122 cyclic group Chemical group 0.000 claims description 2
125000005117 dialkylcarbamoyl group Chemical group 0.000 claims description 2
125000001153 fluoro group Chemical group F* 0.000 claims description 2
125000005842 heteroatom Chemical group 0.000 claims description 2
ORTFAQDWJHRMNX-UHFFFAOYSA-M oxidooxomethyl Chemical compound [O-][C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-M 0.000 claims description 2
239000001301 oxygen Substances 0.000 claims description 2
235000019260 propionic acid Nutrition 0.000 claims description 2
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 2
229910052717 sulfur Inorganic materials 0.000 claims description 2
125000005505 thiomorpholino group Chemical group 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims 8
230000003301 hydrolyzing effect Effects 0.000 claims 2
101100490437 Mus musculus Acvrl1 gene Proteins 0.000 claims 1
239000004480 active ingredient Substances 0.000 claims 1
125000002950 monocyclic group Chemical group 0.000 claims 1
125000003367 polycyclic group Chemical group 0.000 claims 1
229940126601 medicinal product Drugs 0.000 abstract description 3
125000005338 substituted cycloalkoxy group Chemical group 0.000 abstract description 2
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 270
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 171
239000000243 solution Substances 0.000 description 129
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 105
239000003921 oil Substances 0.000 description 88
235000019198 oils Nutrition 0.000 description 88
238000003786 synthesis reaction Methods 0.000 description 86
238000000746 purification Methods 0.000 description 83
238000001953 recrystallisation Methods 0.000 description 76
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 75
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 74
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 68
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 66
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 64
239000000203 mixture Substances 0.000 description 64
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 61
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 51
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
239000000725 suspension Substances 0.000 description 44
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 42
239000000047 product Substances 0.000 description 42
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 38
239000012074 organic phase Substances 0.000 description 38
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 37
229910052943 magnesium sulfate Inorganic materials 0.000 description 37
235000019341 magnesium sulphate Nutrition 0.000 description 37
NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 36
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 36
CPPGZWWUPFWALU-UHFFFAOYSA-N 1-isocyanato-3-methylbenzene Chemical compound CC1=CC=CC(N=C=O)=C1 CPPGZWWUPFWALU-UHFFFAOYSA-N 0.000 description 34
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 34
238000004587 chromatography analysis Methods 0.000 description 33
RHZBRCQIKQUQHQ-UHFFFAOYSA-N 2-(1,3-dioxoisoindol-2-yl)acetyl chloride Chemical compound C1=CC=C2C(=O)N(CC(=O)Cl)C(=O)C2=C1 RHZBRCQIKQUQHQ-UHFFFAOYSA-N 0.000 description 32
239000000377 silicon dioxide Substances 0.000 description 31
BNWCETAHAJSBFG-UHFFFAOYSA-N tert-butyl 2-bromoacetate Chemical compound CC(C)(C)OC(=O)CBr BNWCETAHAJSBFG-UHFFFAOYSA-N 0.000 description 30
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 27
239000003480 eluent Substances 0.000 description 27
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 26
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 24
239000011541 reaction mixture Substances 0.000 description 24
238000010992 reflux Methods 0.000 description 24
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 23
238000001914 filtration Methods 0.000 description 23
239000012312 sodium hydride Substances 0.000 description 23
229910000104 sodium hydride Inorganic materials 0.000 description 23
238000006243 chemical reaction Methods 0.000 description 22
239000008346 aqueous phase Substances 0.000 description 21
239000002904 solvent Substances 0.000 description 21
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 18
125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 18
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 18
125000005518 carboxamido group Chemical group 0.000 description 17
239000000706 filtrate Substances 0.000 description 17
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 15
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 15
239000012442 inert solvent Substances 0.000 description 15
CRFJYELVKLMGKZ-UHFFFAOYSA-N 2-(1,3-dioxoisoindol-2-yl)-n-[2-(trifluoromethoxy)phenyl]acetamide Chemical compound FC(F)(F)OC1=CC=CC=C1NC(=O)CN1C(=O)C2=CC=CC=C2C1=O CRFJYELVKLMGKZ-UHFFFAOYSA-N 0.000 description 14
ZFNNTHBYEFIGBU-UHFFFAOYSA-N tert-butyl 2-[n-[2-(1,3-dioxoisoindol-2-yl)acetyl]-2-(trifluoromethoxy)anilino]acetate Chemical compound O=C1C2=CC=CC=C2C(=O)N1CC(=O)N(CC(=O)OC(C)(C)C)C1=CC=CC=C1OC(F)(F)F ZFNNTHBYEFIGBU-UHFFFAOYSA-N 0.000 description 14
239000012300 argon atmosphere Substances 0.000 description 13
229910000030 sodium bicarbonate Inorganic materials 0.000 description 13
235000017557 sodium bicarbonate Nutrition 0.000 description 13
YLDILLQKQASWBA-UHFFFAOYSA-N 2-bromo-n-methyl-n-phenylacetamide Chemical compound BrCC(=O)N(C)C1=CC=CC=C1 YLDILLQKQASWBA-UHFFFAOYSA-N 0.000 description 12
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 12
RMNOJBAXSNPCBO-UHFFFAOYSA-N tert-butyl 2-[n-(2-aminoacetyl)-2-(trifluoromethoxy)anilino]acetate Chemical compound CC(C)(C)OC(=O)CN(C(=O)CN)C1=CC=CC=C1OC(F)(F)F RMNOJBAXSNPCBO-UHFFFAOYSA-N 0.000 description 12
239000012043 crude product Substances 0.000 description 11
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 9
UVOLVYSEZMBVNY-UHFFFAOYSA-N tert-butyl 2-(3-chloroanilino)acetate Chemical compound CC(C)(C)OC(=O)CNC1=CC=CC(Cl)=C1 UVOLVYSEZMBVNY-UHFFFAOYSA-N 0.000 description 9
FVWOBEFJCTYFMF-UHFFFAOYSA-N tert-butyl 2-(n-(2-aminoacetyl)-3-chloroanilino)acetate Chemical compound CC(C)(C)OC(=O)CN(C(=O)CN)C1=CC=CC(Cl)=C1 FVWOBEFJCTYFMF-UHFFFAOYSA-N 0.000 description 9
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 8
230000007062 hydrolysis Effects 0.000 description 8
238000006460 hydrolysis reaction Methods 0.000 description 8
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 8
239000007787 solid Substances 0.000 description 8
VZOMJJJMNAGVRE-UHFFFAOYSA-N 2-[(3-methylphenyl)carbamoylamino]acetic acid Chemical compound CC1=CC=CC(NC(=O)NCC(O)=O)=C1 VZOMJJJMNAGVRE-UHFFFAOYSA-N 0.000 description 7
DYDKAEUJBSHUAB-UHFFFAOYSA-N 2-isocyanato-n-(3-methoxyphenyl)-n-[2-(n-methylanilino)-2-oxoethyl]acetamide Chemical compound COC1=CC=CC(N(CC(=O)N(C)C=2C=CC=CC=2)C(=O)CN=C=O)=C1 DYDKAEUJBSHUAB-UHFFFAOYSA-N 0.000 description 7
239000002585 base Substances 0.000 description 7
NVVXILVLXODELG-UHFFFAOYSA-N tert-butyl 2-[n-(2-aminoacetyl)-2-(3,3-dimethylpiperidine-1-carbonyl)anilino]acetate Chemical compound CC(C)(C)OC(=O)CN(C(=O)CN)C1=CC=CC=C1C(=O)N1CC(C)(C)CCC1 NVVXILVLXODELG-UHFFFAOYSA-N 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 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
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
230000006978 adaptation Effects 0.000 description 6
ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 6
238000001816 cooling Methods 0.000 description 6
XXONARVVPRQZSS-UHFFFAOYSA-N ethyl 2-[[2-(1,3-dioxoisoindol-2-yl)acetyl]amino]benzoate Chemical compound CCOC(=O)C1=CC=CC=C1NC(=O)CN1C(=O)C2=CC=CC=C2C1=O XXONARVVPRQZSS-UHFFFAOYSA-N 0.000 description 6
GOJJMGCERTUCPU-UHFFFAOYSA-N ethyl 3-[[2-(1,3-dioxoisoindol-2-yl)acetyl]amino]benzoate Chemical compound CCOC(=O)C1=CC=CC(NC(=O)CN2C(C3=CC=CC=C3C2=O)=O)=C1 GOJJMGCERTUCPU-UHFFFAOYSA-N 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
XQWPAKXOXAWOMN-UHFFFAOYSA-N n-[2-(3,3-dimethylpiperidine-1-carbonyl)phenyl]-2-(1,3-dioxoisoindol-2-yl)acetamide Chemical compound C1C(C)(C)CCCN1C(=O)C1=CC=CC=C1NC(=O)CN1C(=O)C2=CC=CC=C2C1=O XQWPAKXOXAWOMN-UHFFFAOYSA-N 0.000 description 6
239000003208 petroleum Substances 0.000 description 6
CPFGICKCTMHNFU-UHFFFAOYSA-N tert-butyl 2-(2,3-dichloroanilino)acetate Chemical compound CC(C)(C)OC(=O)CNC1=CC=CC(Cl)=C1Cl CPFGICKCTMHNFU-UHFFFAOYSA-N 0.000 description 6
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
FWPIDFUJEMBDLS-UHFFFAOYSA-L tin(II) chloride dihydrate Chemical compound O.O.Cl[Sn]Cl FWPIDFUJEMBDLS-UHFFFAOYSA-L 0.000 description 6
OEMDJZJZEDWQDU-UHFFFAOYSA-N 2-(1,3-dioxoisoindol-2-yl)-n-[2-(2-fluoro-n-methylanilino)-2-oxoethyl]-n-(3-methoxyphenyl)acetamide Chemical compound COC1=CC=CC(N(CC(=O)N(C)C=2C(=CC=CC=2)F)C(=O)CN2C(C3=CC=CC=C3C2=O)=O)=C1 OEMDJZJZEDWQDU-UHFFFAOYSA-N 0.000 description 5
102100025841 Cholecystokinin Human genes 0.000 description 5
101800001982 Cholecystokinin Proteins 0.000 description 5
150000007513 acids Chemical class 0.000 description 5
229910052783 alkali metal Inorganic materials 0.000 description 5
238000009835 boiling Methods 0.000 description 5
229940107137 cholecystokinin Drugs 0.000 description 5
125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 5
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YLUAGGVEQDHVMT-UHFFFAOYSA-N tert-butyl 2-(2-chloro-n-[2-[(3-methylphenyl)carbamoylamino]acetyl]anilino)acetate Chemical compound CC1=CC=CC(NC(=O)NCC(=O)N(CC(=O)OC(C)(C)C)C=2C(=CC=CC=2)Cl)=C1 YLUAGGVEQDHVMT-UHFFFAOYSA-N 0.000 description 1
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OAUHSDAYYNHISQ-UHFFFAOYSA-N tert-butyl 2-(n-[2-(1,3-dioxoisoindol-2-yl)acetyl]-2-methoxyanilino)acetate Chemical compound COC1=CC=CC=C1N(CC(=O)OC(C)(C)C)C(=O)CN1C(=O)C2=CC=CC=C2C1=O OAUHSDAYYNHISQ-UHFFFAOYSA-N 0.000 description 1
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HKXARGHQHKXGOT-UHFFFAOYSA-N tert-butyl 2-[2-(3,3-dimethylpiperidine-1-carbonyl)-n-[2-[(3-methylphenyl)carbamoylamino]acetyl]anilino]acetate Chemical compound CC1=CC=CC(NC(=O)NCC(=O)N(CC(=O)OC(C)(C)C)C=2C(=CC=CC=2)C(=O)N2CC(C)(C)CCC2)=C1 HKXARGHQHKXGOT-UHFFFAOYSA-N 0.000 description 1
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XTLWIEPMRSTWSN-UHFFFAOYSA-N tert-butyl 2-[4-(dimethylamino)-N-[2-[(3-methylsulfanylphenyl)carbamoylamino]acetyl]anilino]acetate Chemical compound CN(C1=CC=C(C=C1)N(C(CNC(=O)NC1=CC(=CC=C1)SC)=O)CC(=O)OC(C)(C)C)C XTLWIEPMRSTWSN-UHFFFAOYSA-N 0.000 description 1
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HXWMCBNCVMVADP-UHFFFAOYSA-N tert-butyl 2-[n-[2-[(3-methylphenyl)carbamoylamino]acetyl]-3-(trifluoromethoxy)anilino]acetate Chemical compound CC1=CC=CC(NC(=O)NCC(=O)N(CC(=O)OC(C)(C)C)C=2C=C(OC(F)(F)F)C=CC=2)=C1 HXWMCBNCVMVADP-UHFFFAOYSA-N 0.000 description 1
SPWQBJJTLPJSKW-UHFFFAOYSA-N tert-butyl 2-[n-[2-[(3-methylphenyl)carbamoylamino]acetyl]-3-(trifluoromethyl)anilino]acetate Chemical compound CC1=CC=CC(NC(=O)NCC(=O)N(CC(=O)OC(C)(C)C)C=2C=C(C=CC=2)C(F)(F)F)=C1 SPWQBJJTLPJSKW-UHFFFAOYSA-N 0.000 description 1
ZAMBDUNVPATALL-UHFFFAOYSA-N tert-butyl 2-[n-[2-[(3-methylphenyl)carbamoylamino]acetyl]-3-(trifluoromethylsulfanyl)anilino]acetate Chemical compound CC1=CC=CC(NC(=O)NCC(=O)N(CC(=O)OC(C)(C)C)C=2C=C(SC(F)(F)F)C=CC=2)=C1 ZAMBDUNVPATALL-UHFFFAOYSA-N 0.000 description 1
LYDRKKWPKKEMNZ-UHFFFAOYSA-N tert-butyl benzoate Chemical group CC(C)(C)OC(=O)C1=CC=CC=C1 LYDRKKWPKKEMNZ-UHFFFAOYSA-N 0.000 description 1
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238000011200 topical administration Methods 0.000 description 1
239000002966 varnish Substances 0.000 description 1
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