CS241039B2 - Method of new n-(2-(or 3)pyrrolidinyle(or pyrrolidinylmethyl)((-benzamides production,substituted in positions 2,3,4,5,6 - Google Patents
Method of new n-(2-(or 3)pyrrolidinyle(or pyrrolidinylmethyl)((-benzamides production,substituted in positions 2,3,4,5,6 Download PDFInfo
- Publication number
- CS241039B2 CS241039B2 CS8380A CS8083A CS241039B2 CS 241039 B2 CS241039 B2 CS 241039B2 CS 8380 A CS8380 A CS 8380A CS 8083 A CS8083 A CS 8083A CS 241039 B2 CS241039 B2 CS 241039B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- carbon atoms
- formula
- group
- pyrrolidinylmethyl
- methoxy
- Prior art date
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- -1 pyrrolidinylmethyl Chemical group 0.000 title claims description 39
- 238000000034 method Methods 0.000 title claims description 7
- 229940054066 benzamide antipsychotics Drugs 0.000 title claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 29
- 150000001875 compounds Chemical class 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 10
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 8
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
- 150000007513 acids Chemical class 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- 150000001408 amides Chemical group 0.000 claims description 2
- 150000003936 benzamides Chemical group 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000005153 alkyl sulfamoyl group Chemical group 0.000 claims 2
- 125000003368 amide group Chemical group 0.000 claims 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 1
- 239000005711 Benzoic acid Substances 0.000 claims 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 1
- 235000010233 benzoic acid Nutrition 0.000 claims 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 claims 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical group [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims 1
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 claims 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 239000013078 crystal Substances 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 238000001914 filtration Methods 0.000 description 5
- ATGSLQBVSZNJMT-UHFFFAOYSA-N 2,5-dichloropentan-1-amine;hydrochloride Chemical compound Cl.NCC(Cl)CCCCl ATGSLQBVSZNJMT-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- LHGHUKINGVHMJJ-UHFFFAOYSA-N 4-amino-n-[[1-(cyclopropylmethyl)pyrrolidin-2-yl]methyl]-5-ethylsulfonyl-2-methoxybenzamide Chemical compound C1=C(N)C(S(=O)(=O)CC)=CC(C(=O)NCC2N(CCC2)CC2CC2)=C1OC LHGHUKINGVHMJJ-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- NKBOUJFQADABIY-UHFFFAOYSA-N CCS(=O)(=O)CCOC(=O)C1=CC(=C(C=C1N)OC)C(=O)O Chemical compound CCS(=O)(=O)CCOC(=O)C1=CC(=C(C=C1N)OC)C(=O)O NKBOUJFQADABIY-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- CPLWIGOCCLYPGK-UHFFFAOYSA-N n-[(1-cyclopropylpyrrolidin-2-yl)methyl]-2-methoxy-5-sulfamoylbenzamide Chemical compound COC1=CC=C(S(N)(=O)=O)C=C1C(=O)NCC1N(C2CC2)CCC1 CPLWIGOCCLYPGK-UHFFFAOYSA-N 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 2
- QTWZISKLRIHFNO-UHFFFAOYSA-N n-(2,5-dichloropentyl)-2-methoxy-5-sulfamoylbenzamide Chemical compound COC1=CC=C(S(N)(=O)=O)C=C1C(=O)NCC(Cl)CCCCl QTWZISKLRIHFNO-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 1
- OAMHTTBNEJBIKA-UHFFFAOYSA-N 2,2,2-trichloro-1-phenylethanone Chemical compound ClC(Cl)(Cl)C(=O)C1=CC=CC=C1 OAMHTTBNEJBIKA-UHFFFAOYSA-N 0.000 description 1
- SQAILWDRVDGLGY-UHFFFAOYSA-N 2-methoxy-5-sulfamoylbenzoic acid Chemical compound COC1=CC=C(S(N)(=O)=O)C=C1C(O)=O SQAILWDRVDGLGY-UHFFFAOYSA-N 0.000 description 1
- XFZMCFJADJFEBB-UHFFFAOYSA-N 2-methoxy-5-sulfamoylbenzoyl chloride Chemical compound COC1=CC=C(S(N)(=O)=O)C=C1C(Cl)=O XFZMCFJADJFEBB-UHFFFAOYSA-N 0.000 description 1
- MXBLZLWZAHUKLU-UHFFFAOYSA-N 2-sulfamoylbenzamide Chemical compound NC(=O)C1=CC=CC=C1S(N)(=O)=O MXBLZLWZAHUKLU-UHFFFAOYSA-N 0.000 description 1
- OJVNCXHGGYYOPH-UHFFFAOYSA-N 4-amino-5-ethylsulfonyl-2-methoxybenzoic acid Chemical compound CCS(=O)(=O)C1=CC(C(O)=O)=C(OC)C=C1N OJVNCXHGGYYOPH-UHFFFAOYSA-N 0.000 description 1
- PFXOJRCOFMOPTK-UHFFFAOYSA-N 4-amino-n-(2,5-dichloropentyl)-5-ethylsulfonyl-2-methoxybenzamide Chemical compound CCS(=O)(=O)C1=CC(C(=O)NCC(Cl)CCCCl)=C(OC)C=C1N PFXOJRCOFMOPTK-UHFFFAOYSA-N 0.000 description 1
- RDZJTCROLXNZCL-UHFFFAOYSA-N 4-amino-n-[(1-cyclopentylpyrrolidin-2-yl)methyl]-5-ethylsulfinyl-2-methoxybenzamide Chemical compound C1=C(N)C(S(=O)CC)=CC(C(=O)NCC2N(CCC2)C2CCCC2)=C1OC RDZJTCROLXNZCL-UHFFFAOYSA-N 0.000 description 1
- KKERKXFIBOXOMB-UHFFFAOYSA-N 4-amino-n-[1-(cyclohexylmethyl)pyrrolidin-3-yl]-5-ethylsulfonyl-2-methoxybenzamide Chemical compound C1=C(N)C(S(=O)(=O)CC)=CC(C(=O)NC2CN(CC3CCCCC3)CC2)=C1OC KKERKXFIBOXOMB-UHFFFAOYSA-N 0.000 description 1
- OMIXTXLVXNSKCW-UHFFFAOYSA-N 4-amino-n-[[1-(cyclohexylmethyl)pyrrolidin-2-yl]methyl]-5-ethylsulfonyl-2-methoxybenzamide Chemical compound C1=C(N)C(S(=O)(=O)CC)=CC(C(=O)NCC2N(CCC2)CC2CCCCC2)=C1OC OMIXTXLVXNSKCW-UHFFFAOYSA-N 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
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 150000001204 N-oxides Chemical class 0.000 description 1
- SHMJZRLQZJEDDL-UHFFFAOYSA-N N1(CCCC1)CC1=C(C(=C(C(=O)N)C=C1S(N)(=O)=O)OC)OC Chemical compound N1(CCCC1)CC1=C(C(=C(C(=O)N)C=C1S(N)(=O)=O)OC)OC SHMJZRLQZJEDDL-UHFFFAOYSA-N 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 150000001540 azides Chemical class 0.000 description 1
- SNIABFMMCKVXSY-UHFFFAOYSA-N benzoylazanium;chloride Chemical compound Cl.NC(=O)C1=CC=CC=C1 SNIABFMMCKVXSY-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- IGSKHXTUVXSOMB-UHFFFAOYSA-N cyclopropylmethanamine Chemical compound NCC1CC1 IGSKHXTUVXSOMB-UHFFFAOYSA-N 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- HBGGXOJOCNVPFY-UHFFFAOYSA-N diisononyl phthalate Chemical compound CC(C)CCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCC(C)C HBGGXOJOCNVPFY-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 150000002540 isothiocyanates Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- PTTMZJCWHXWNMI-UHFFFAOYSA-N n-[(1-cyclohexylpyrrolidin-2-yl)methyl]-2-methoxy-5-(methylsulfamoyl)benzamide Chemical compound CNS(=O)(=O)C1=CC=C(OC)C(C(=O)NCC2N(CCC2)C2CCCCC2)=C1 PTTMZJCWHXWNMI-UHFFFAOYSA-N 0.000 description 1
- MPVPYQCWTVLWAB-UHFFFAOYSA-N n-[(1-cyclopentylpyrrolidin-2-yl)methyl]-2,4-dimethoxy-5-methylsulfonylbenzamide Chemical compound COC1=CC(OC)=C(S(C)(=O)=O)C=C1C(=O)NCC1N(C2CCCC2)CCC1 MPVPYQCWTVLWAB-UHFFFAOYSA-N 0.000 description 1
- MHAJIJIZSZAWAS-UHFFFAOYSA-N n-[1-(cyclohexylmethyl)pyrrolidin-3-yl]-2-methoxy-5-methylsulfonylbenzamide Chemical compound COC1=CC=C(S(C)(=O)=O)C=C1C(=O)NC1CN(CC2CCCCC2)CC1 MHAJIJIZSZAWAS-UHFFFAOYSA-N 0.000 description 1
- JJFAEKOMPRJYCI-UHFFFAOYSA-N n-[[1-(cyclohexylmethyl)pyrrolidin-2-yl]methyl]-2-methoxy-6-methyl-3-propan-2-yl-5-sulfamoylbenzamide Chemical compound COC1=C(C(C)C)C=C(S(N)(=O)=O)C(C)=C1C(=O)NCC1N(CC2CCCCC2)CCC1 JJFAEKOMPRJYCI-UHFFFAOYSA-N 0.000 description 1
- URRSYDOURLSJKC-UHFFFAOYSA-N n-[[1-(cyclopropylmethyl)pyrrolidin-2-yl]methyl]-2,3-dimethoxy-5-sulfamoylbenzamide Chemical compound COC1=CC(S(N)(=O)=O)=CC(C(=O)NCC2N(CCC2)CC2CC2)=C1OC URRSYDOURLSJKC-UHFFFAOYSA-N 0.000 description 1
- CFCMKIXHYZJCGX-UHFFFAOYSA-N n-[[1-(cyclopropylmethyl)pyrrolidin-2-yl]methyl]-2,4-dimethoxy-5-methylsulfonylbenzamide Chemical compound COC1=CC(OC)=C(S(C)(=O)=O)C=C1C(=O)NCC1N(CC2CC2)CCC1 CFCMKIXHYZJCGX-UHFFFAOYSA-N 0.000 description 1
- NJKYHQTVJOWOLH-UHFFFAOYSA-N n-[[1-(cyclopropylmethyl)pyrrolidin-2-yl]methyl]-2-methoxy-6-methyl-3-propan-2-yl-5-sulfamoylbenzamide Chemical compound COC1=C(C(C)C)C=C(S(N)(=O)=O)C(C)=C1C(=O)NCC1N(CC2CC2)CCC1 NJKYHQTVJOWOLH-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical class C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/14—Nitrogen atoms not forming part of a nitro radical
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/08—Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/21—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/21—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups
- C07C65/28—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups having unsaturation outside the aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
- C07D207/09—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Psychiatry (AREA)
- Hospice & Palliative Care (AREA)
- Otolaryngology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pyrrole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7801633A FR2424909A1 (fr) | 1978-01-20 | 1978-01-20 | Nouveaux derives d'ortho-anisamides utiles comme medicaments modificateurs du comportement, et leurs procedes de preparation |
| FR7831458A FR2440946A2 (fr) | 1978-01-20 | 1978-11-07 | Nouveaux benzamides heterocycliques substitues, leurs procedes de preparation et leur application comme modificateurs du comportement |
| CS79444A CS241016B2 (en) | 1978-01-20 | 1979-01-19 | Method of new n-(2-(or)pyrrolidinylmethyl)-benzamides production substituted in positions 2,3,4,5,6 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS8083A2 CS8083A2 (en) | 1985-06-13 |
| CS241039B2 true CS241039B2 (en) | 1986-03-13 |
Family
ID=26220412
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS79444A CS241016B2 (en) | 1978-01-20 | 1979-01-19 | Method of new n-(2-(or)pyrrolidinylmethyl)-benzamides production substituted in positions 2,3,4,5,6 |
| CS8380A CS241039B2 (en) | 1978-01-20 | 1979-01-19 | Method of new n-(2-(or 3)pyrrolidinyle(or pyrrolidinylmethyl)((-benzamides production,substituted in positions 2,3,4,5,6 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS79444A CS241016B2 (en) | 1978-01-20 | 1979-01-19 | Method of new n-(2-(or)pyrrolidinylmethyl)-benzamides production substituted in positions 2,3,4,5,6 |
Country Status (39)
| Country | Link |
|---|---|
| US (2) | US4673686A (hu) |
| JP (1) | JPS54138553A (hu) |
| AR (2) | AR221355A1 (hu) |
| AT (2) | AT377254B (hu) |
| AU (1) | AU520746B2 (hu) |
| BE (1) | BE873522A (hu) |
| BG (2) | BG48335A3 (hu) |
| CA (1) | CA1133477A (hu) |
| CH (2) | CH639369A5 (hu) |
| CS (2) | CS241016B2 (hu) |
| CY (1) | CY1202A (hu) |
| DD (1) | DD141521A5 (hu) |
| DE (1) | DE2901170A1 (hu) |
| DK (1) | DK157008C (hu) |
| EG (1) | EG13764A (hu) |
| ES (2) | ES476757A1 (hu) |
| FI (1) | FI69833C (hu) |
| FR (1) | FR2440946A2 (hu) |
| GB (2) | GB2013662B (hu) |
| GR (1) | GR64398B (hu) |
| HK (1) | HK12284A (hu) |
| HU (1) | HU177902B (hu) |
| IE (2) | IE48209B1 (hu) |
| IL (2) | IL56413A (hu) |
| IN (1) | IN150618B (hu) |
| IT (1) | IT1164821B (hu) |
| LU (1) | LU80793A1 (hu) |
| MC (1) | MC1231A1 (hu) |
| MX (2) | MX6192E (hu) |
| NL (1) | NL7900455A (hu) |
| NO (1) | NO153530C (hu) |
| NZ (2) | NZ189381A (hu) |
| OA (1) | OA06153A (hu) |
| PL (1) | PL117195B1 (hu) |
| PT (1) | PT69069A (hu) |
| RO (2) | RO76554A (hu) |
| SE (2) | SE449862B (hu) |
| SU (1) | SU1158040A3 (hu) |
| YU (2) | YU41608B (hu) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE8101536L (sv) * | 1981-03-11 | 1982-09-12 | Astra Laekemedel Ab | Bensamid-derivat |
| SE8205135D0 (sv) * | 1982-09-09 | 1982-09-09 | Astra Laekemedel Ab | Benzamido-derivatives |
| CH656126A5 (de) * | 1983-08-18 | 1986-06-13 | Ciba Geigy Ag | Durch 2-propynyloxygruppen substituierte phthalsaeureanhydride. |
| SE8400478D0 (sv) * | 1984-01-31 | 1984-01-31 | Astra Laekemedel Ab | Oxysalicylamido derivatives |
| US5240957A (en) * | 1984-01-31 | 1993-08-31 | Astra Lakemedel Akteibolag | Oxysalicylamido derivatives |
| FR2574795B1 (fr) * | 1984-12-18 | 1987-11-20 | Ile De France | Nouveau procede industriel de synthese du n-((1'-allyl 2'-pyrrolidinyl) methyl) 2-methoxy 4,5-azimido benzamide |
| FR2586018B1 (fr) * | 1985-08-12 | 1988-03-25 | Ile De France | Nouveau benzodioxepanne, son procede de synthese et ses applications en therapeutique |
| US4772459A (en) * | 1986-09-09 | 1988-09-20 | Erbamont, Inc. | Method for controlling emesis caused by chemotherapeutic agents and antiemetic agents useful therein |
| US5154913A (en) * | 1987-11-19 | 1992-10-13 | Vanderbilt University | Radioiodinated benzamines method of their use as radioimaging agents |
| EP0320630A1 (en) * | 1987-11-19 | 1989-06-21 | The Vanderbilt University | Enantiometric iodobenzamides |
| CA2036516A1 (en) * | 1990-02-19 | 1991-08-20 | Yoshikazu Asahina | Optically active 8-methoxyouinolonecarboxylic acid derivatives, their preparative processes and their intermediates |
| FR2678266A1 (fr) * | 1991-06-28 | 1992-12-31 | Delagrange Laboratoires | Nouveaux derives de 2-hydroxy 4-amino 5-ethylsulfonyl benzamide utiles comme anxiolytiques. |
| US5993777A (en) * | 1993-05-06 | 1999-11-30 | Research Corporation Technologies, Inc. | Benzamide compounds for cancer imaging and therapy |
| US5911970A (en) * | 1993-05-06 | 1999-06-15 | Research Corporation Technologies, Inc. | Methods for cancer imaging and therapy using benzamine compounds |
| US6517811B2 (en) | 1993-05-06 | 2003-02-11 | Research Corporation Technologies, Inc. | Compounds for cancer imaging and therapy |
| WO1994026314A1 (en) * | 1993-05-06 | 1994-11-24 | John Christy S | Compounds for cancer imaging and therapy |
| CN103450058B (zh) * | 2013-09-18 | 2015-10-14 | 广安凯特医药化工有限公司 | 一种氨磺必利酸的制备方法 |
| CN105503666A (zh) * | 2015-12-30 | 2016-04-20 | 苏州诚和医药化学有限公司 | 一种便捷合成2-甲氧基-5-氨磺酰基苯甲酸甲酯的方法 |
Family Cites Families (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3342826A (en) * | 1964-01-13 | 1967-09-19 | Ile De France | Heterocyclic aminoalkyl benzamides |
| FR6787M (hu) * | 1967-08-17 | 1969-03-17 | ||
| US3891671A (en) * | 1968-08-01 | 1975-06-24 | Ile De France | N-(2-pyrrolidyl or piperidyl alkyl)-4-hydroxy benzamides |
| US3959477A (en) * | 1968-08-01 | 1976-05-25 | Societe D'etudes Scientifiques Et Industrielles De L'ile-De-France | Methods of protection against emesis in mammals by administration of a heterocyclic benzamide |
| GB1364231A (en) * | 1968-12-23 | 1974-08-21 | Robins Co Inc A H | N-/1-substituted-3-pyrrolidinyl/benzamides and thiobenzamides |
| US3577440A (en) * | 1968-12-23 | 1971-05-04 | Robins Co Inc A H | 1-substituted-3-amido-pyrrolidines |
| FR2097031A1 (en) * | 1970-07-29 | 1972-03-03 | Berri Balzac | 2-aminoethoxyethyl-6,6-dimethyl nor pinane derivs - local anaesthetics spasmolytics and anticholinergics |
| GB1392194A (en) * | 1971-09-23 | 1975-04-30 | Wyeth John & Brother Ltd | Pyrrolidine derivatives |
| US4279822A (en) * | 1972-04-03 | 1981-07-21 | A. H. Robins Company, Inc. | N-(1-Substituted-3-pyrrolidinyl)benzamides |
| US3966957A (en) * | 1972-04-03 | 1976-06-29 | A. H. Robins Company, Incorporated | Method for controlling emesis with N-(1-substituted-3-pyrrolidinyl)benzamides and thiobenzamides |
| US3862139A (en) * | 1972-06-23 | 1975-01-21 | Delmar Chem | Heterocyclic benzamide compounds |
| US4048321A (en) * | 1973-12-14 | 1977-09-13 | Science Union Et Cie | Disubstituted azabicycloalkanes |
| CH605793A5 (hu) * | 1974-03-05 | 1978-10-13 | Ile De France | |
| CA1039731A (en) * | 1974-12-18 | 1978-10-03 | Synthelabo | Process for preparing new 2-methoxy-benzamide derivatives |
| US4158060A (en) * | 1974-12-18 | 1979-06-12 | Synthelabo | 2-Methoxy-benzamide derivatives |
| US4172143A (en) * | 1974-12-18 | 1979-10-23 | Synthelabo | 2-Methoxy-benzamide derivatives |
| US4039672A (en) * | 1975-01-11 | 1977-08-02 | Societe D'etudes Scientifiques Et Industrielles De L'ile-De-France | N-(1'-allypyrrolidinyl 2'-methyl) 2-methoxy 4,5-azimido benzamide and its pharmaceutically acceptable salts |
| GB1520584A (en) * | 1975-04-02 | 1978-08-09 | Yamanouchi Pharma Co Ltd | 2 - alkoxy - 5 substituted benzamide derivatives and their use in pharmaceutical compositions |
| US4197243A (en) * | 1975-04-02 | 1980-04-08 | Yamanouchi Pharmaceutical Co., Ltd. | N-1-Benzyl-3-pyrrolidinyl-4-dimethylamino benzamide derivatives |
| CH614709A5 (hu) * | 1975-09-25 | 1979-12-14 | Ciba Geigy Ag | |
| JPS5248661A (en) * | 1975-10-14 | 1977-04-18 | Synthelabo | 22methoxyybenzamide derivatives |
| NZ186175A (en) * | 1977-01-27 | 1980-03-05 | Shionogi & Co | Meta-sulphonamidobenzamide derivatives |
| FR2415099A1 (fr) * | 1978-01-20 | 1979-08-17 | Ile De France | Nouveaux derives de 4-amino-5-alkylsulfonyl ortho-anisamides, leurs procedes de preparation et leur application comme psychotropes |
| IL61642A0 (en) * | 1979-12-20 | 1981-01-30 | Beecham Group Ltd | Aniline derivatives,their preparation and pharmalceutical compositions containing them |
| IL61972A0 (en) * | 1980-01-30 | 1981-02-27 | Beecham Group Ltd | Azabicyclic compounds,their preparation and pharmaceutical compositions containing them |
| US4352802A (en) * | 1980-06-10 | 1982-10-05 | Beecham Group Limited | Bicyclo[3.3.1]nonyl-benzamide |
| FR2493848B2 (fr) * | 1980-11-07 | 1986-05-16 | Delalande Sa | Nouveaux derives des nor-tropane et granatane, leur procede de preparation et leur application en therapeutique |
-
1978
- 1978-11-07 FR FR7831458A patent/FR2440946A2/fr active Granted
-
1979
- 1979-01-11 ES ES476757A patent/ES476757A1/es not_active Expired
- 1979-01-11 IL IL56413A patent/IL56413A/xx unknown
- 1979-01-11 AR AR275135A patent/AR221355A1/es active
- 1979-01-11 MC MC791354A patent/MC1231A1/xx unknown
- 1979-01-12 PT PT69069A patent/PT69069A/pt unknown
- 1979-01-13 DE DE19792901170 patent/DE2901170A1/de active Granted
- 1979-01-15 BG BG042076A patent/BG48335A3/xx unknown
- 1979-01-15 GR GR58091A patent/GR64398B/el unknown
- 1979-01-15 BG BG043504A patent/BG48336A3/xx unknown
- 1979-01-15 NZ NZ189381A patent/NZ189381A/en unknown
- 1979-01-15 AU AU43374/79A patent/AU520746B2/en not_active Ceased
- 1979-01-16 LU LU80793A patent/LU80793A1/xx unknown
- 1979-01-17 GB GB7901688A patent/GB2013662B/en not_active Expired
- 1979-01-17 GB GB8119940A patent/GB2083459B/en not_active Expired
- 1979-01-17 EG EG28/79A patent/EG13764A/xx active
- 1979-01-17 BE BE1/9242A patent/BE873522A/xx not_active IP Right Cessation
- 1979-01-17 YU YU105/79A patent/YU41608B/xx unknown
- 1979-01-17 SE SE7900419A patent/SE449862B/sv not_active IP Right Cessation
- 1979-01-17 CY CY1202A patent/CY1202A/xx unknown
- 1979-01-17 IN IN46/CAL/79A patent/IN150618B/en unknown
- 1979-01-18 CH CH50979A patent/CH639369A5/fr not_active IP Right Cessation
- 1979-01-18 RO RO7996327A patent/RO76554A/ro unknown
- 1979-01-18 IT IT47707/79A patent/IT1164821B/it active
- 1979-01-18 DK DK021079A patent/DK157008C/da not_active IP Right Cessation
- 1979-01-18 RO RO79103351A patent/RO80716A/ro unknown
- 1979-01-18 NO NO790179A patent/NO153530C/no unknown
- 1979-01-19 PL PL1979212898A patent/PL117195B1/pl unknown
- 1979-01-19 SU SU792712702A patent/SU1158040A3/ru active
- 1979-01-19 CS CS79444A patent/CS241016B2/cs unknown
- 1979-01-19 OA OA56713A patent/OA06153A/xx unknown
- 1979-01-19 NL NL7900455A patent/NL7900455A/xx not_active Application Discontinuation
- 1979-01-19 AT AT0039779A patent/AT377254B/de not_active IP Right Cessation
- 1979-01-19 CS CS8380A patent/CS241039B2/cs unknown
- 1979-01-19 DD DD79210558A patent/DD141521A5/de unknown
- 1979-01-19 JP JP548479A patent/JPS54138553A/ja active Granted
- 1979-01-19 MX MX797670U patent/MX6192E/es unknown
- 1979-01-19 HU HU79SO1242A patent/HU177902B/hu not_active IP Right Cessation
- 1979-01-19 MX MX7911207U patent/MX7622E/es unknown
- 1979-01-19 CA CA319,968A patent/CA1133477A/en not_active Expired
- 1979-01-19 FI FI790181A patent/FI69833C/fi not_active IP Right Cessation
- 1979-01-30 IE IE2021/81A patent/IE48209B1/en not_active IP Right Cessation
- 1979-01-30 IE IE91/79A patent/IE48208B1/en not_active IP Right Cessation
- 1979-02-16 ES ES477783A patent/ES477783A1/es not_active Expired
-
1980
- 1980-07-10 AR AR281712A patent/AR221428A1/es active
-
1981
- 1981-03-04 NZ NZ196409A patent/NZ196409A/xx unknown
-
1982
- 1982-02-03 IL IL64928A patent/IL64928A0/xx not_active IP Right Cessation
- 1982-12-03 YU YU2685/82A patent/YU43809B/xx unknown
-
1983
- 1983-05-26 CH CH289083A patent/CH641154A5/fr not_active IP Right Cessation
- 1983-08-24 AT AT0301483A patent/AT377979B/de not_active IP Right Cessation
-
1984
- 1984-02-16 HK HK122/84A patent/HK12284A/xx unknown
-
1985
- 1985-08-26 US US06/769,796 patent/US4673686A/en not_active Expired - Fee Related
-
1986
- 1986-04-30 US US06/858,906 patent/US4816471A/en not_active Expired - Fee Related
- 1986-10-16 SE SE8604394A patent/SE463972B/sv not_active IP Right Cessation
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