GB1560019A - 2-methoxy-benzamides - Google Patents
2-methoxy-benzamides Download PDFInfo
- Publication number
- GB1560019A GB1560019A GB48451/77A GB4845177A GB1560019A GB 1560019 A GB1560019 A GB 1560019A GB 48451/77 A GB48451/77 A GB 48451/77A GB 4845177 A GB4845177 A GB 4845177A GB 1560019 A GB1560019 A GB 1560019A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methoxy
- pyrrolidinylmethyl
- compound
- racemate
- optical isomer
- Prior art date
- 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.)
- Expired
Links
- MNWSGMTUGXNYHJ-UHFFFAOYSA-N 2-methoxybenzamide Chemical class COC1=CC=CC=C1C(N)=O MNWSGMTUGXNYHJ-UHFFFAOYSA-N 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 29
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 13
- -1 N - (1 - Cyclopropylmethyl - 2 - pyrrolidinylmethyl)-2-methoxy-5-methylsulphonylbenzamide Chemical compound 0.000 claims description 12
- 230000003287 optical effect Effects 0.000 claims description 11
- ILUJQPXNXACGAN-UHFFFAOYSA-N O-methylsalicylic acid Chemical compound COC1=CC=CC=C1C(O)=O ILUJQPXNXACGAN-UHFFFAOYSA-N 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 6
- 241000699670 Mus sp. Species 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 241000282472 Canis lupus familiaris Species 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 230000003474 anti-emetic effect Effects 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- 230000008485 antagonism Effects 0.000 claims description 3
- VMWNQDUVQKEIOC-CYBMUJFWSA-N apomorphine Chemical compound C([C@H]1N(C)CC2)C3=CC=C(O)C(O)=C3C3=C1C2=CC=C3 VMWNQDUVQKEIOC-CYBMUJFWSA-N 0.000 claims description 3
- 229960004046 apomorphine Drugs 0.000 claims description 3
- 150000004820 halides Chemical class 0.000 claims description 3
- DQAPWKHZPNVZSW-UHFFFAOYSA-N n-[[1-(cyclopentylmethyl)pyrrolidin-2-yl]methyl]-2-methoxy-5-sulfamoylbenzamide Chemical compound COC1=CC=C(S(N)(=O)=O)C=C1C(=O)NCC1N(CC2CCCC2)CCC1 DQAPWKHZPNVZSW-UHFFFAOYSA-N 0.000 claims description 3
- BTYDXWCTJDAEHA-UHFFFAOYSA-N n-[[1-(cyclopropylmethyl)pyrrolidin-2-yl]methyl]-2-methoxy-5-sulfamoylbenzamide Chemical compound COC1=CC=C(S(N)(=O)=O)C=C1C(=O)NCC1N(CC2CC2)CCC1 BTYDXWCTJDAEHA-UHFFFAOYSA-N 0.000 claims description 3
- 230000000701 neuroleptic effect Effects 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 208000019695 Migraine disease Diseases 0.000 claims description 2
- 206010028813 Nausea Diseases 0.000 claims description 2
- 208000008469 Peptic Ulcer Diseases 0.000 claims description 2
- 208000028017 Psychotic disease Diseases 0.000 claims description 2
- 206010047700 Vomiting Diseases 0.000 claims description 2
- 125000005907 alkyl ester group Chemical group 0.000 claims description 2
- 230000003354 anti-apomorphinic effect Effects 0.000 claims description 2
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 claims description 2
- 230000003001 depressive effect Effects 0.000 claims description 2
- 208000002173 dizziness Diseases 0.000 claims description 2
- 230000000694 effects Effects 0.000 claims description 2
- 230000000095 emetic effect Effects 0.000 claims description 2
- 231100000029 gastro-duodenal ulcer Toxicity 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 206010027599 migraine Diseases 0.000 claims description 2
- QNPMCZYJCKYDII-UHFFFAOYSA-N n-[[1-(cyclobutylmethyl)pyrrolidin-2-yl]methyl]-2-methoxy-5-sulfamoylbenzamide Chemical compound COC1=CC=C(S(N)(=O)=O)C=C1C(=O)NCC1N(CC2CCC2)CCC1 QNPMCZYJCKYDII-UHFFFAOYSA-N 0.000 claims description 2
- YCFKZUYQGDQHIW-UHFFFAOYSA-N n-[[1-(cyclopropylmethyl)pyrrolidin-2-yl]methyl]-5-(dimethylsulfamoyl)-2-methoxybenzamide Chemical compound COC1=CC=C(S(=O)(=O)N(C)C)C=C1C(=O)NCC1N(CC2CC2)CCC1 YCFKZUYQGDQHIW-UHFFFAOYSA-N 0.000 claims description 2
- QKXNKRVTNUKKHQ-UHFFFAOYSA-N n-[[1-(cyclopropylmethyl)pyrrolidin-2-yl]methyl]-5-ethylsulfonyl-2-methoxybenzamide Chemical compound CCS(=O)(=O)C1=CC=C(OC)C(C(=O)NCC2N(CCC2)CC2CC2)=C1 QKXNKRVTNUKKHQ-UHFFFAOYSA-N 0.000 claims description 2
- 230000008693 nausea Effects 0.000 claims description 2
- 238000007911 parenteral administration Methods 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 230000002265 prevention Effects 0.000 claims description 2
- 208000020016 psychiatric disease Diseases 0.000 claims description 2
- 230000009758 senescence Effects 0.000 claims description 2
- 230000008673 vomiting Effects 0.000 claims description 2
- AUKXFNABVHIUAC-UHFFFAOYSA-N pyrrolidin-2-ylmethylamine Chemical compound NCC1CCCN1 AUKXFNABVHIUAC-UHFFFAOYSA-N 0.000 claims 2
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 25
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
- 239000000203 mixture Substances 0.000 description 24
- 239000007787 solid Substances 0.000 description 21
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 19
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
- 238000002844 melting Methods 0.000 description 15
- 230000008018 melting Effects 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 14
- AFVFQIVMOAPDHO-UHFFFAOYSA-M Methanesulfonate Chemical compound CS([O-])(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 7
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 7
- 235000019341 magnesium sulphate Nutrition 0.000 description 7
- 239000002585 base Substances 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- 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 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 description 3
- 229930182821 L-proline Natural products 0.000 description 3
- QFIYFROFRTUSPW-UHFFFAOYSA-N [1-(cyclopropylmethyl)pyrrolidin-2-yl]methanamine Chemical compound NCC1CCCN1CC1CC1 QFIYFROFRTUSPW-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 150000003235 pyrrolidines Chemical class 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 230000000707 stereoselective effect Effects 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 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 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 229910006074 SO2NH2 Inorganic materials 0.000 description 2
- 229940024606 amino acid Drugs 0.000 description 2
- 235000001014 amino acid Nutrition 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 125000004494 ethyl ester group Chemical group 0.000 description 2
- 239000012280 lithium aluminium hydride Substances 0.000 description 2
- 229960002429 proline Drugs 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- KUZHJDHQWITKMT-ZETCQYMHSA-N (2s)-1-(cyclopropanecarbonyl)pyrrolidine-2-carboxamide Chemical compound NC(=O)[C@@H]1CCCN1C(=O)C1CC1 KUZHJDHQWITKMT-ZETCQYMHSA-N 0.000 description 1
- XXJGBENTLXFVFI-UHFFFAOYSA-N 1-amino-methylene Chemical compound N[CH2] XXJGBENTLXFVFI-UHFFFAOYSA-N 0.000 description 1
- RCFGFTLCCWRMTI-UHFFFAOYSA-N 2-methoxy-5-methylsulfonylbenzoyl chloride Chemical compound COC1=CC=C(S(C)(=O)=O)C=C1C(Cl)=O RCFGFTLCCWRMTI-UHFFFAOYSA-N 0.000 description 1
- KFODYSFLGQDJLD-UHFFFAOYSA-N 5-(dimethylsulfamoyl)-2-methoxybenzoyl chloride Chemical compound COC1=CC=C(S(=O)(=O)N(C)C)C=C1C(Cl)=O KFODYSFLGQDJLD-UHFFFAOYSA-N 0.000 description 1
- HULDRQRKKXRXBI-UHFFFAOYSA-N 5-chloro-2-methoxybenzoic acid Chemical compound COC1=CC=C(Cl)C=C1C(O)=O HULDRQRKKXRXBI-UHFFFAOYSA-N 0.000 description 1
- GSFGGUVBFJQNQQ-UHFFFAOYSA-N 5-ethylsulfonyl-2-methoxybenzoyl chloride Chemical compound CCS(=O)(=O)C1=CC=C(OC)C(C(Cl)=O)=C1 GSFGGUVBFJQNQQ-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
- 101100181033 Caenorhabditis elegans unc-116 gene Proteins 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- ONIBWKKTOPOVIA-SCSAIBSYSA-N D-Proline Chemical compound OC(=O)[C@H]1CCCN1 ONIBWKKTOPOVIA-SCSAIBSYSA-N 0.000 description 1
- 229930182820 D-proline Natural products 0.000 description 1
- WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical compound F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-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
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
- VLJNHYLEOZPXFW-BYPYZUCNSA-N L-prolinamide Chemical compound NC(=O)[C@@H]1CCCN1 VLJNHYLEOZPXFW-BYPYZUCNSA-N 0.000 description 1
- ODHCTXKNWHHXJC-GSVOUGTGSA-N Pyroglutamic acid Natural products OC(=O)[C@H]1CCC(=O)N1 ODHCTXKNWHHXJC-GSVOUGTGSA-N 0.000 description 1
- UZRNNPSYEAYZIK-NSHDSACASA-N [(2s)-1-(cyclopentylmethyl)pyrrolidin-2-yl]methanamine Chemical compound NC[C@@H]1CCCN1CC1CCCC1 UZRNNPSYEAYZIK-NSHDSACASA-N 0.000 description 1
- QFIYFROFRTUSPW-VIFPVBQESA-N [(2s)-1-(cyclopropylmethyl)pyrrolidin-2-yl]methanamine Chemical compound NC[C@@H]1CCCN1CC1CC1 QFIYFROFRTUSPW-VIFPVBQESA-N 0.000 description 1
- HVVNJUAVDAZWCB-YFKPBYRVSA-N [(2s)-pyrrolidin-2-yl]methanol Chemical compound OC[C@@H]1CCCN1 HVVNJUAVDAZWCB-YFKPBYRVSA-N 0.000 description 1
- ODHCTXKNWHHXJC-UHFFFAOYSA-N acide pyroglutamique Natural products OC(=O)C1CCC(=O)N1 ODHCTXKNWHHXJC-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000003936 benzamides Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 230000009194 climbing Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- ZOOSILUVXHVRJE-UHFFFAOYSA-N cyclopropanecarbonyl chloride Chemical compound ClC(=O)C1CC1 ZOOSILUVXHVRJE-UHFFFAOYSA-N 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- QPNJHVDIRZNKOX-LURJTMIESA-N ethyl (2s)-pyrrolidine-2-carboxylate Chemical compound CCOC(=O)[C@@H]1CCCN1 QPNJHVDIRZNKOX-LURJTMIESA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 239000004220 glutamic acid Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- WCAFZWICGDVPKS-UHFFFAOYSA-N n-[[1-(cyclohexylmethyl)pyrrolidin-2-yl]methyl]-2-methoxy-5-sulfamoylbenzamide Chemical compound COC1=CC=C(S(N)(=O)=O)C=C1C(=O)NCC1N(CC2CCCCC2)CCC1 WCAFZWICGDVPKS-UHFFFAOYSA-N 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- LJCNRYVRMXRIQR-OLXYHTOASA-L potassium sodium L-tartrate Chemical compound [Na+].[K+].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O LJCNRYVRMXRIQR-OLXYHTOASA-L 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 239000001476 sodium potassium tartrate Substances 0.000 description 1
- 235000011006 sodium potassium tartrate Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000000565 sulfonamide group Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 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
- 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
- C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyrrole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7717988A FR2394529A2 (fr) | 1977-06-13 | 1977-06-13 | Methoxy-2 benzamides et leur application en therapeutique |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1560019A true GB1560019A (en) | 1980-01-30 |
Family
ID=9192010
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB48451/77A Expired GB1560019A (en) | 1977-06-13 | 1977-11-21 | 2-methoxy-benzamides |
Country Status (10)
| Country | Link |
|---|---|
| JP (1) | JPS545969A (enrdf_load_stackoverflow) |
| AU (1) | AU509543B2 (enrdf_load_stackoverflow) |
| BE (1) | BE861866R (enrdf_load_stackoverflow) |
| FR (1) | FR2394529A2 (enrdf_load_stackoverflow) |
| GB (1) | GB1560019A (enrdf_load_stackoverflow) |
| IE (1) | IE45999B1 (enrdf_load_stackoverflow) |
| IT (1) | IT1206606B (enrdf_load_stackoverflow) |
| LU (1) | LU78681A1 (enrdf_load_stackoverflow) |
| NL (1) | NL7713631A (enrdf_load_stackoverflow) |
| ZA (1) | ZA776950B (enrdf_load_stackoverflow) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1095415B (it) * | 1978-02-16 | 1985-08-10 | Ravizza Spa | Processo per la produzione di una benzamide otticamente attiva,benzamide otticamente attiva cosi'ottenuta e composizioni |
| AU542211B2 (en) * | 1980-03-07 | 1985-02-14 | Gruppo Lepetit S.P.A. | Mercaptocycloalkyl carbonyl prolines |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR5916M (enrdf_load_stackoverflow) * | 1966-01-21 | 1968-05-06 |
-
1977
- 1977-06-13 FR FR7717988A patent/FR2394529A2/fr active Granted
- 1977-11-21 GB GB48451/77A patent/GB1560019A/en not_active Expired
- 1977-11-21 ZA ZA00776950A patent/ZA776950B/xx unknown
- 1977-11-25 IE IE2392/77A patent/IE45999B1/en unknown
- 1977-12-09 NL NL7713631A patent/NL7713631A/xx not_active Application Discontinuation
- 1977-12-13 AU AU31514/77A patent/AU509543B2/en not_active Expired
- 1977-12-13 LU LU78681A patent/LU78681A1/xx unknown
- 1977-12-14 BE BE183469A patent/BE861866R/xx not_active IP Right Cessation
- 1977-12-15 JP JP15158377A patent/JPS545969A/ja active Pending
-
1978
- 1978-05-24 IT IT7823749A patent/IT1206606B/it active
Also Published As
| Publication number | Publication date |
|---|---|
| IT7823749A0 (it) | 1978-05-24 |
| BE861866R (fr) | 1978-06-14 |
| JPS545969A (en) | 1979-01-17 |
| IE45999L (en) | 1978-12-13 |
| ZA776950B (en) | 1978-09-27 |
| NL7713631A (nl) | 1978-12-15 |
| IT1206606B (it) | 1989-04-27 |
| AU509543B2 (en) | 1980-05-15 |
| FR2394529A2 (fr) | 1979-01-12 |
| AU3151477A (en) | 1979-06-21 |
| LU78681A1 (enrdf_load_stackoverflow) | 1978-07-11 |
| FR2394529B2 (enrdf_load_stackoverflow) | 1980-01-18 |
| IE45999B1 (en) | 1983-01-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] |