CA2040151A1 - Composes a base d'acide phenylsulfonylalcanoique - Google Patents

Composes a base d'acide phenylsulfonylalcanoique

Info

Publication number: CA2040151A1
Authority: CA; Canada
Prior art keywords: carbon atoms; group; acid; compounds; alkyl group
Prior art date: 1991-04-08
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Abandoned

Application number

CA 2040151

Other languages

English (en)

Inventor

Makio Kitazawa

Masuo Akahane

Yasushi Nakano

Atsushi Tsubaki

Kazuaki Sato

Masaaki Ban

Michihiro Kobayashi

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Kissei Pharmaceutical Co Ltd

Original Assignee

Kissei Pharmaceutical Co Ltd

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1991-04-08

Filing date

1991-04-10

Publication date

1992-10-11

1991-04-08 Priority claimed from EP91303079A external-priority patent/EP0508004A1/fr

1991-04-10 Application filed by Kissei Pharmaceutical Co Ltd filed Critical Kissei Pharmaceutical Co Ltd

1991-04-10 Priority to CA 2040151 priority Critical patent/CA2040151A1/fr

1992-10-11 Publication of CA2040151A1 publication Critical patent/CA2040151A1/fr

Status Abandoned legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 78
239000002253 acid Substances 0.000 title claims abstract description 30
150000003839 salts Chemical class 0.000 claims abstract description 14
125000004432 carbon atom Chemical group C* 0.000 claims description 37
125000000217 alkyl group Chemical group 0.000 claims description 26
125000003710 aryl alkyl group Chemical group 0.000 claims description 8
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 6
125000005843 halogen group Chemical group 0.000 claims description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
239000004480 active ingredient Substances 0.000 claims description 2
239000008194 pharmaceutical composition Substances 0.000 claims description 2
206010033645 Pancreatitis Diseases 0.000 abstract description 4
206010033647 Pancreatitis acute Diseases 0.000 abstract description 4
201000003229 acute pancreatitis Diseases 0.000 abstract description 4
208000003770 biliary dyskinesia Diseases 0.000 abstract description 4
208000002551 irritable bowel syndrome Diseases 0.000 abstract description 4
230000002265 prevention Effects 0.000 abstract description 4
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 57
239000000243 solution Substances 0.000 description 54
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 36
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 33
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
239000003921 oil Substances 0.000 description 33
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 30
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 30
238000003756 stirring Methods 0.000 description 27
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 26
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 26
239000011541 reaction mixture Substances 0.000 description 25
101150041968 CDC13 gene Proteins 0.000 description 20
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 19
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 19
229910052943 magnesium sulfate Inorganic materials 0.000 description 17
229960001701 chloroform Drugs 0.000 description 16
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 16
235000019341 magnesium sulphate Nutrition 0.000 description 15
239000000377 silicon dioxide Substances 0.000 description 15
GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 14
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 13
238000003818 flash chromatography Methods 0.000 description 13
239000000203 mixture Substances 0.000 description 13
NQPDZGIKBAWPEJ-UHFFFAOYSA-M valerate Chemical compound CCCCC([O-])=O NQPDZGIKBAWPEJ-UHFFFAOYSA-M 0.000 description 13
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 11
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
-1 amino acid compounds Chemical class 0.000 description 8
229910052739 hydrogen Inorganic materials 0.000 description 8
239000012044 organic layer Substances 0.000 description 8
238000010609 cell counting kit-8 assay Methods 0.000 description 7
239000003814 drug Substances 0.000 description 7
238000002844 melting Methods 0.000 description 7
230000008018 melting Effects 0.000 description 7
IZTQOLKUZKXIRV-YRVFCXMDSA-N sincalide Chemical compound C([C@@H](C(=O)N[C@@H](CCSC)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](N)CC(O)=O)C1=CC=C(OS(O)(=O)=O)C=C1 IZTQOLKUZKXIRV-YRVFCXMDSA-N 0.000 description 7
235000010265 sodium sulphite Nutrition 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
RKOTXQYWCBGZLP-UHFFFAOYSA-N N-[(2,4-difluorophenyl)methyl]-2-ethyl-9-hydroxy-3-methoxy-1,8-dioxospiro[3H-pyrido[1,2-a]pyrazine-4,3'-oxolane]-7-carboxamide Chemical compound CCN1C(OC)C2(CCOC2)N2C=C(C(=O)NCC3=C(F)C=C(F)C=C3)C(=O)C(O)=C2C1=O RKOTXQYWCBGZLP-UHFFFAOYSA-N 0.000 description 6
108010087230 Sincalide Proteins 0.000 description 6
238000000921 elemental analysis Methods 0.000 description 6
235000019260 propionic acid Nutrition 0.000 description 6
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 description 6
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 6
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
239000000047 product Substances 0.000 description 5
QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 4
239000004382 Amylase Substances 0.000 description 4
102000013142 Amylases Human genes 0.000 description 4
108010065511 Amylases Proteins 0.000 description 4
102000004859 Cholecystokinin Receptors Human genes 0.000 description 4
108090001085 Cholecystokinin Receptors Proteins 0.000 description 4
235000019418 amylase Nutrition 0.000 description 4
230000003042 antagnostic effect Effects 0.000 description 4
230000027455 binding Effects 0.000 description 4
229940079593 drug Drugs 0.000 description 4
ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 4
210000000232 gallbladder Anatomy 0.000 description 4
230000028327 secretion Effects 0.000 description 4
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
230000008602 contraction Effects 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
238000000034 method Methods 0.000 description 3
210000000496 pancreas Anatomy 0.000 description 3
102000005962 receptors Human genes 0.000 description 3
108020003175 receptors Proteins 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
239000011734 sodium Substances 0.000 description 3
239000002904 solvent Substances 0.000 description 3
229940124597 therapeutic agent Drugs 0.000 description 3
XAMKSQSIPPAYLA-UHFFFAOYSA-N 2-[(3,4-dichlorophenyl)sulfanylmethyl]-5-methoxy-5-oxopentanoic acid Chemical compound COC(=O)CCC(C(O)=O)CSC1=CC=C(Cl)C(Cl)=C1 XAMKSQSIPPAYLA-UHFFFAOYSA-N 0.000 description 2
VQPFOMRSQNHPQB-UHFFFAOYSA-N 2-[(3,4-dichlorophenyl)sulfanylmethyl]pentanedinitrile Chemical compound ClC1=CC=C(SCC(CCC#N)C#N)C=C1Cl VQPFOMRSQNHPQB-UHFFFAOYSA-N 0.000 description 2
NGCJVMZXRCLPRQ-UHFFFAOYSA-N 2-methylidenepentanedinitrile Chemical compound N#CC(=C)CCC#N NGCJVMZXRCLPRQ-UHFFFAOYSA-N 0.000 description 2
HNJZDPKMMZXSKT-UHFFFAOYSA-N 3,4-dichlorobenzenethiol Chemical compound SC1=CC=C(Cl)C(Cl)=C1 HNJZDPKMMZXSKT-UHFFFAOYSA-N 0.000 description 2
TVADYQZCBVCKSS-UHFFFAOYSA-N 5-methoxy-2-methyl-5-oxopentanoic acid Chemical compound COC(=O)CCC(C)C(O)=O TVADYQZCBVCKSS-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 description 2
241000700157 Rattus norvegicus Species 0.000 description 2
125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
239000000872 buffer Substances 0.000 description 2
210000000170 cell membrane Anatomy 0.000 description 2
LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 description 2
238000004440 column chromatography Methods 0.000 description 2
238000001816 cooling Methods 0.000 description 2
239000013078 crystal Substances 0.000 description 2
DRJWHYQGOSTPNS-UHFFFAOYSA-N ditert-butyl 2-[(3,4-dichlorophenyl)sulfanylmethyl]hexanedioate Chemical compound CC(C)(C)OC(=O)CCCC(C(=O)OC(C)(C)C)CSC1=CC=C(Cl)C(Cl)=C1 DRJWHYQGOSTPNS-UHFFFAOYSA-N 0.000 description 2
239000002552 dosage form Substances 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
239000010410 layer Substances 0.000 description 2
FQJSWFYPNWZWHC-UHFFFAOYSA-N methyl 4-[(3,4-dimethylphenyl)sulfanylmethyl]-5-(dipentylamino)-5-oxopentanoate Chemical compound CCCCCN(CCCCC)C(=O)C(CCC(=O)OC)CSC1=CC=C(C)C(C)=C1 FQJSWFYPNWZWHC-UHFFFAOYSA-N 0.000 description 2
230000003287 optical effect Effects 0.000 description 2
239000008188 pellet Substances 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
238000012746 preparative thin layer chromatography Methods 0.000 description 2
LOUPRKONTZGTKE-LHHVKLHASA-N quinidine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@H]2[C@@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-LHHVKLHASA-N 0.000 description 2
150000003385 sodium Chemical class 0.000 description 2
230000009870 specific binding Effects 0.000 description 2
238000010561 standard procedure Methods 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
RFQIIVWUNOGSRR-UHFFFAOYSA-N 2-[(3,4-dichlorophenyl)sulfanylmethyl]-4-methoxy-4-oxobutanoic acid Chemical compound COC(=O)CC(C(O)=O)CSC1=CC=C(Cl)C(Cl)=C1 RFQIIVWUNOGSRR-UHFFFAOYSA-N 0.000 description 1
HPYVEBOBWCYJOC-UHFFFAOYSA-N 2-[(3,4-dichlorophenyl)sulfanylmethyl]-6-methoxy-6-oxohexanoic acid Chemical compound COC(=O)CCCC(C(O)=O)CSC1=CC=C(Cl)C(Cl)=C1 HPYVEBOBWCYJOC-UHFFFAOYSA-N 0.000 description 1
JNRJUDKSOVDRCZ-UHFFFAOYSA-N 2-[(3,4-dichlorophenyl)sulfanylmethyl]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)CSC1=CC=C(Cl)C(Cl)=C1 JNRJUDKSOVDRCZ-UHFFFAOYSA-N 0.000 description 1
QKOSUQDUCCGQAV-UHFFFAOYSA-N 2-[(3,4-dimethylphenyl)sulfanylmethyl]-5-methoxy-5-oxopentanoic acid Chemical compound COC(=O)CCC(C(O)=O)CSC1=CC=C(C)C(C)=C1 QKOSUQDUCCGQAV-UHFFFAOYSA-N 0.000 description 1
NICCSHFMHHBRNI-UHFFFAOYSA-N 2-[(3,4-dimethylphenyl)sulfanylmethyl]pentanedinitrile Chemical compound CC1=CC=C(SCC(CCC#N)C#N)C=C1C NICCSHFMHHBRNI-UHFFFAOYSA-N 0.000 description 1
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
IDKCKPBAFOIONK-UHFFFAOYSA-N 3,4-dimethylbenzenethiol Chemical compound CC1=CC=C(S)C=C1C IDKCKPBAFOIONK-UHFFFAOYSA-N 0.000 description 1
WMKNPRYHQYLNIA-UHFFFAOYSA-N 4-[(3,4-dichlorophenyl)sulfonylmethyl]-5-(dipentylamino)-5-oxopentanoic acid Chemical compound CCCCCN(CCCCC)C(=O)C(CCC(O)=O)CS(=O)(=O)C1=CC=C(Cl)C(Cl)=C1 WMKNPRYHQYLNIA-UHFFFAOYSA-N 0.000 description 1
XELPFXSFGHBNSV-UHFFFAOYSA-N 4-[(3,4-dichlorophenyl)sulfonylmethyl]-5-oxo-5-[pentyl(2-phenylethyl)amino]pentanoic acid Chemical compound C=1C=C(Cl)C(Cl)=CC=1S(=O)(=O)CC(CCC(O)=O)C(=O)N(CCCCC)CCC1=CC=CC=C1 XELPFXSFGHBNSV-UHFFFAOYSA-N 0.000 description 1
SNCZZUCIIAORCA-UHFFFAOYSA-N 4-[(4-acetylphenyl)sulfonylmethyl]-5-(dipentylamino)-5-oxopentanoic acid Chemical compound CCCCCN(CCCCC)C(=O)C(CCC(O)=O)CS(=O)(=O)C1=CC=C(C(C)=O)C=C1 SNCZZUCIIAORCA-UHFFFAOYSA-N 0.000 description 1
JRLTTZUODKEYDH-UHFFFAOYSA-N 8-methylquinoline Chemical group C1=CN=C2C(C)=CC=CC2=C1 JRLTTZUODKEYDH-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
239000004475 Arginine Substances 0.000 description 1
241000182988 Assa Species 0.000 description 1
108010001478 Bacitracin Proteins 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
101710125089 Bindin Proteins 0.000 description 1
108091003079 Bovine Serum Albumin Proteins 0.000 description 1
241000700199 Cavia porcellus Species 0.000 description 1
101800001982 Cholecystokinin Proteins 0.000 description 1
102100025841 Cholecystokinin Human genes 0.000 description 1
235000001258 Cinchona calisaya Nutrition 0.000 description 1
102100033933 Endoplasmic reticulum protein SC65 Human genes 0.000 description 1
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
101000639962 Homo sapiens Endoplasmic reticulum protein SC65 Proteins 0.000 description 1
ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 1
CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 description 1
239000002841 Lewis acid Substances 0.000 description 1
239000002879 Lewis base Substances 0.000 description 1
241000700159 Rattus Species 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
101100073357 Streptomyces halstedii sch2 gene Proteins 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 1
210000000577 adipose tissue Anatomy 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
235000001014 amino acid Nutrition 0.000 description 1
JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
230000008485 antagonism Effects 0.000 description 1
ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
235000003704 aspartic acid Nutrition 0.000 description 1
238000003556 assay Methods 0.000 description 1
239000012131 assay buffer Substances 0.000 description 1
239000012911 assay medium Substances 0.000 description 1
229960003071 bacitracin Drugs 0.000 description 1
229930184125 bacitracin Natural products 0.000 description 1
CLKOFPXJLQSYAH-ABRJDSQDSA-N bacitracin A Chemical compound C1SC([C@@H](N)[C@@H](C)CC)=N[C@@H]1C(=O)N[C@@H](CC(C)C)C(=O)N[C@H](CCC(O)=O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H]1C(=O)N[C@H](CCCN)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CC=2N=CNC=2)C(=O)N[C@H](CC(O)=O)C(=O)N[C@@H](CC(N)=O)C(=O)NCCCC1 CLKOFPXJLQSYAH-ABRJDSQDSA-N 0.000 description 1
239000002585 base Substances 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
229940098773 bovine serum albumin Drugs 0.000 description 1
159000000007 calcium salts Chemical class 0.000 description 1
239000002775 capsule Substances 0.000 description 1
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
125000005587 carbonate group Chemical group 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
229940107137 cholecystokinin Drugs 0.000 description 1
210000001953 common bile duct Anatomy 0.000 description 1
125000004093 cyano group Chemical group *C#N 0.000 description 1
SPWVRYZQLGQKGK-UHFFFAOYSA-N dichloromethane;hexane Chemical compound ClCCl.CCCCCC SPWVRYZQLGQKGK-UHFFFAOYSA-N 0.000 description 1
229960003887 dichlorophen Drugs 0.000 description 1
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
GTSOXTFEZJAODX-UHFFFAOYSA-N ditert-butyl 2-methylidenehexanedioate Chemical compound CC(C)(C)OC(=O)CCCC(=C)C(=O)OC(C)(C)C GTSOXTFEZJAODX-UHFFFAOYSA-N 0.000 description 1
VHJLVAABSRFDPM-QWWZWVQMSA-N dithiothreitol Chemical compound SC[C@@H](O)[C@H](O)CS VHJLVAABSRFDPM-QWWZWVQMSA-N 0.000 description 1
235000011389 fruit/vegetable juice Nutrition 0.000 description 1
239000003629 gastrointestinal hormone Substances 0.000 description 1
239000003365 glass fiber Substances 0.000 description 1
235000013922 glutamic acid Nutrition 0.000 description 1
239000004220 glutamic acid Substances 0.000 description 1
239000008187 granular material Substances 0.000 description 1
238000000265 homogenisation Methods 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
238000011534 incubation Methods 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000006229 isopropoxyethyl group Chemical group [H]C([H])([H])C([H])(OC([H])([H])C([H])([H])*)C([H])([H])[H] 0.000 description 1
150000007517 lewis acids Chemical class 0.000 description 1
150000007527 lewis bases Chemical class 0.000 description 1
239000000463 material Substances 0.000 description 1
239000002609 medium Substances 0.000 description 1
MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
NDGZHIUFDIKANI-UHFFFAOYSA-N methyl 4-[(3,4-dichlorophenyl)sulfanylmethyl]-5-(dipentylamino)-5-oxopentanoate Chemical compound CCCCCN(CCCCC)C(=O)C(CCC(=O)OC)CSC1=CC=C(Cl)C(Cl)=C1 NDGZHIUFDIKANI-UHFFFAOYSA-N 0.000 description 1
OLAOOIYUMDWILA-UHFFFAOYSA-N methyl 4-[(3,4-dichlorophenyl)sulfinylmethyl]-5-(dipentylamino)-5-oxopentanoate Chemical compound CCCCCN(CCCCC)C(=O)C(CCC(=O)OC)CS(=O)C1=CC=C(Cl)C(Cl)=C1 OLAOOIYUMDWILA-UHFFFAOYSA-N 0.000 description 1
OQABOXQLBLCERU-UHFFFAOYSA-N methyl 4-[(3,4-dichlorophenyl)sulfonylmethyl]-5-oxo-5-[pentyl(2-phenylethyl)amino]pentanoate Chemical compound C=1C=C(Cl)C(Cl)=CC=1S(=O)(=O)CC(CCC(=O)OC)C(=O)N(CCCCC)CCC1=CC=CC=C1 OQABOXQLBLCERU-UHFFFAOYSA-N 0.000 description 1
BVJNGHBYHAOOLD-UHFFFAOYSA-N methyl 4-[(3,4-dimethylphenyl)sulfinylmethyl]-5-(dipentylamino)-5-oxopentanoate Chemical compound CCCCCN(CCCCC)C(=O)C(CCC(=O)OC)CS(=O)C1=CC=C(C)C(C)=C1 BVJNGHBYHAOOLD-UHFFFAOYSA-N 0.000 description 1
RNYZVWPRPXGHDZ-UHFFFAOYSA-N methyl 4-[(4-acetylphenyl)sulfanylmethyl]-5-(dipentylamino)-5-oxopentanoate Chemical compound CCCCCN(CCCCC)C(=O)C(CCC(=O)OC)CSC1=CC=C(C(C)=O)C=C1 RNYZVWPRPXGHDZ-UHFFFAOYSA-N 0.000 description 1
ZDMWAQIUMISYBP-UHFFFAOYSA-N methyl 5-(dipentylamino)-4-[(4-methylphenyl)sulfinylmethyl]-5-oxopentanoate Chemical compound CCCCCN(CCCCC)C(=O)C(CCC(=O)OC)CS(=O)C1=CC=C(C)C=C1 ZDMWAQIUMISYBP-UHFFFAOYSA-N 0.000 description 1
NFJMCKQQJUJUEL-UHFFFAOYSA-N methyl 5-[benzyl(methyl)amino]-4-[(3,4-dichlorophenyl)sulfanylmethyl]-5-oxopentanoate Chemical compound C=1C=CC=CC=1CN(C)C(=O)C(CCC(=O)OC)CSC1=CC=C(Cl)C(Cl)=C1 NFJMCKQQJUJUEL-UHFFFAOYSA-N 0.000 description 1
HTSHRNPPRKUOTE-UHFFFAOYSA-N methyl 5-[benzyl(methyl)amino]-4-[(3,4-dichlorophenyl)sulfonylmethyl]-5-oxopentanoate Chemical compound C=1C=CC=CC=1CN(C)C(=O)C(CCC(=O)OC)CS(=O)(=O)C1=CC=C(Cl)C(Cl)=C1 HTSHRNPPRKUOTE-UHFFFAOYSA-N 0.000 description 1
238000000465 moulding Methods 0.000 description 1
JACMPVXHEARCBO-UHFFFAOYSA-N n-pentylpentan-1-amine Chemical compound CCCCCNCCCCC JACMPVXHEARCBO-UHFFFAOYSA-N 0.000 description 1
230000009871 nonspecific binding Effects 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
125000005429 oxyalkyl group Chemical group 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
125000004344 phenylpropyl group Chemical group 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
239000006187 pill Substances 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
229960003857 proglumide Drugs 0.000 description 1
229960001404 quinidine Drugs 0.000 description 1
229960000948 quinine Drugs 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
VLQWXUDCWYBQBM-UHFFFAOYSA-M sodium;4-methoxy-2-methylidene-4-oxobutanoate Chemical compound [Na+].COC(=O)CC(=C)C([O-])=O VLQWXUDCWYBQBM-UHFFFAOYSA-M 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000010254 subcutaneous injection Methods 0.000 description 1
239000007929 subcutaneous injection Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000003826 tablet Substances 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical class SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 1
GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 1

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

CA 2040151 1991-04-08 1991-04-10 Composes a base d'acide phenylsulfonylalcanoique Abandoned CA2040151A1 (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA 2040151 CA2040151A1 (fr)	1991-04-08	1991-04-10	Composes a base d'acide phenylsulfonylalcanoique

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
EP91303079A EP0508004A1 (fr)	1991-04-08	1991-04-08	Composés d'acide phénylsulfonylalkanoique
CA 2040151 CA2040151A1 (fr)	1991-04-08	1991-04-10	Composes a base d'acide phenylsulfonylalcanoique

Publications (1)

Publication Number	Publication Date
CA2040151A1 true CA2040151A1 (fr)	1992-10-11

Family

ID=25674548

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA 2040151 Abandoned CA2040151A1 (fr)	1991-04-08	1991-04-10	Composes a base d'acide phenylsulfonylalcanoique

Country Status (1)

Country	Link
CA (1)	CA2040151A1 (fr)

1991
- 1991-04-10 CA CA 2040151 patent/CA2040151A1/fr not_active Abandoned

Legal Events

Date	Code	Title	Description
1994-10-10	FZDE	Dead

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