NO121213B - - Google Patents
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- Publication number
- NO121213B NO121213B NO265268A NO265268A NO121213B NO 121213 B NO121213 B NO 121213B NO 265268 A NO265268 A NO 265268A NO 265268 A NO265268 A NO 265268A NO 121213 B NO121213 B NO 121213B
- Authority
- NO
- Norway
- Prior art keywords
- amide
- formula
- meaning
- anthranilic acid
- group
- Prior art date
Links
- 150000001408 amides Chemical class 0.000 claims description 17
- 150000008064 anhydrides Chemical class 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical group NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 claims description 5
- 150000004985 diamines Chemical class 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000003368 amide group Chemical group 0.000 claims description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 2
- 239000005977 Ethylene Substances 0.000 claims description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 150000001448 anilines Chemical class 0.000 claims description 2
- 150000003936 benzamides Chemical class 0.000 claims description 2
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
- 125000004185 ester group Chemical group 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 38
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 36
- 238000009835 boiling Methods 0.000 description 35
- 238000002844 melting Methods 0.000 description 35
- 230000008018 melting Effects 0.000 description 35
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
- 239000000203 mixture Substances 0.000 description 17
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-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
- 238000010992 reflux Methods 0.000 description 9
- 239000002253 acid Substances 0.000 description 8
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 7
- 238000001816 cooling Methods 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- 241000699670 Mus sp. Species 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 6
- OROGSEYTTFOCAN-DNJOTXNNSA-N codeine Chemical compound C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC OROGSEYTTFOCAN-DNJOTXNNSA-N 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 5
- 239000006227 byproduct Substances 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
- -1 N-substituted anthranilic acids Chemical class 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- IIQWRPKYRRGQGQ-UHFFFAOYSA-N CN(CCNC(C=1C(NC2=C(C=CC=C2)C)=CC=CC1)=O)C Chemical compound CN(CCNC(C=1C(NC2=C(C=CC=C2)C)=CC=CC1)=O)C IIQWRPKYRRGQGQ-UHFFFAOYSA-N 0.000 description 3
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 3
- 229960004126 codeine Drugs 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- OROGSEYTTFOCAN-UHFFFAOYSA-N hydrocodone Natural products C1C(N(CCC234)C)C2C=CC(O)C3OC2=C4C1=CC=C2OC OROGSEYTTFOCAN-UHFFFAOYSA-N 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- WPLOMMLAKZRMLC-UHFFFAOYSA-N 2-(3-chloro-2-methylanilino)-N-[3-(dimethylamino)propyl]benzamide Chemical compound CN(CCCNC(C=1C(NC2=C(C(=CC=C2)Cl)C)=CC=CC1)=O)C WPLOMMLAKZRMLC-UHFFFAOYSA-N 0.000 description 2
- BYAQVQHPZHTOAG-UHFFFAOYSA-N 2-chloro-n-[2-(dimethylamino)ethyl]benzamide Chemical compound CN(C)CCNC(=O)C1=CC=CC=C1Cl BYAQVQHPZHTOAG-UHFFFAOYSA-N 0.000 description 2
- ZUVPLKVDZNDZCM-UHFFFAOYSA-N 3-chloro-2-methylaniline Chemical compound CC1=C(N)C=CC=C1Cl ZUVPLKVDZNDZCM-UHFFFAOYSA-N 0.000 description 2
- CEGGKPQRDVTOJL-UHFFFAOYSA-N CN(CCNC(C=1C(NC2=C(C(=CC=C2)Cl)C)=CC=CC1)=O)C Chemical compound CN(CCNC(C=1C(NC2=C(C(=CC=C2)Cl)C)=CC=CC1)=O)C CEGGKPQRDVTOJL-UHFFFAOYSA-N 0.000 description 2
- ABDLHWYOHSFLQG-UHFFFAOYSA-N CN(CCNC(C=1C(NC2=CC(=CC=C2)C)=CC=CC1)=O)C Chemical compound CN(CCNC(C=1C(NC2=CC(=CC=C2)C)=CC=CC1)=O)C ABDLHWYOHSFLQG-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical class NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- DRJNEOPSLFNNDH-UHFFFAOYSA-N N-[3-(dimethylamino)propyl]-2-[3-(trifluoromethyl)anilino]benzamide Chemical compound CN(CCCNC(C=1C(NC2=CC(=CC=C2)C(F)(F)F)=CC=CC1)=O)C DRJNEOPSLFNNDH-UHFFFAOYSA-N 0.000 description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
- 230000000202 analgesic effect Effects 0.000 description 2
- 230000001754 anti-pyretic effect Effects 0.000 description 2
- 239000002221 antipyretic Substances 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 150000001860 citric acid derivatives Chemical class 0.000 description 2
- 150000003840 hydrochlorides Chemical class 0.000 description 2
- DILRJUIACXKSQE-UHFFFAOYSA-N n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCN DILRJUIACXKSQE-UHFFFAOYSA-N 0.000 description 2
- BMWACDPPGXNGFD-UHFFFAOYSA-N n-[3-(dimethylamino)propyl]-2-(2,3-dimethylanilino)benzamide Chemical compound CN(C)CCCNC(=O)C1=CC=CC=C1NC1=CC=CC(C)=C1C BMWACDPPGXNGFD-UHFFFAOYSA-N 0.000 description 2
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 2
- 238000007911 parenteral administration Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 208000011580 syndromic disease Diseases 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- YEZNLOUZAIOMLT-UHFFFAOYSA-N tolfenamic acid Chemical compound CC1=C(Cl)C=CC=C1NC1=CC=CC=C1C(O)=O YEZNLOUZAIOMLT-UHFFFAOYSA-N 0.000 description 2
- WTYQLHHATZZNKW-UHFFFAOYSA-N 2-(3-chloroanilino)-N-[2-(dimethylamino)ethyl]benzamide Chemical compound CN(CCNC(C=1C(NC2=CC(=CC=C2)Cl)=CC=CC=1)=O)C WTYQLHHATZZNKW-UHFFFAOYSA-N 0.000 description 1
- HGYUHWSJYDHPDG-UHFFFAOYSA-N 2-(3-chloroanilino)-N-[2-(dimethylamino)propyl]benzamide Chemical compound CN(C(CNC(C=1C(NC2=CC(=CC=C2)Cl)=CC=CC1)=O)C)C HGYUHWSJYDHPDG-UHFFFAOYSA-N 0.000 description 1
- JODCQKTVDXZQEP-UHFFFAOYSA-N 2-(3-methylanilino)benzoic acid Chemical compound CC1=CC=CC(NC=2C(=CC=CC=2)C(O)=O)=C1 JODCQKTVDXZQEP-UHFFFAOYSA-N 0.000 description 1
- PCMWIMRKWLFADG-UHFFFAOYSA-N 2-chloro-n-[3-(dimethylamino)propyl]benzamide Chemical compound CN(C)CCCNC(=O)C1=CC=CC=C1Cl PCMWIMRKWLFADG-UHFFFAOYSA-N 0.000 description 1
- VIUDTWATMPPKEL-UHFFFAOYSA-N 3-(trifluoromethyl)aniline Chemical compound NC1=CC=CC(C(F)(F)F)=C1 VIUDTWATMPPKEL-UHFFFAOYSA-N 0.000 description 1
- RMMXTBMQSGEXHJ-UHFFFAOYSA-N Aminophenazone Chemical compound O=C1C(N(C)C)=C(C)N(C)N1C1=CC=CC=C1 RMMXTBMQSGEXHJ-UHFFFAOYSA-N 0.000 description 1
- QRFGSAYXJUYVOQ-UHFFFAOYSA-N C(C)N(CCCNC(C=1C(NC2=C(C=CC=C2)Cl)=CC=CC1)=O)CC Chemical compound C(C)N(CCCNC(C=1C(NC2=C(C=CC=C2)Cl)=CC=CC1)=O)CC QRFGSAYXJUYVOQ-UHFFFAOYSA-N 0.000 description 1
- YGJQEWGCUCUEJN-UHFFFAOYSA-N C(C)N(CCCNC(C=1C(NC2=CC(=CC=C2)Cl)=CC=CC1)=O)CC Chemical compound C(C)N(CCCNC(C=1C(NC2=CC(=CC=C2)Cl)=CC=CC1)=O)CC YGJQEWGCUCUEJN-UHFFFAOYSA-N 0.000 description 1
- AUJNUKLRIVEKTK-UHFFFAOYSA-N CC(CNC(=O)C1=CC=CC=C1NC1=C(C)C=CC=C1)N(C)C Chemical compound CC(CNC(=O)C1=CC=CC=C1NC1=C(C)C=CC=C1)N(C)C AUJNUKLRIVEKTK-UHFFFAOYSA-N 0.000 description 1
- ZAJPYUQVYGQECG-UHFFFAOYSA-N CN(C(CNC(C=1C(NC2=C(C(=CC=C2)C)Cl)=CC=CC1)=O)C)C Chemical compound CN(C(CNC(C=1C(NC2=C(C(=CC=C2)C)Cl)=CC=CC1)=O)C)C ZAJPYUQVYGQECG-UHFFFAOYSA-N 0.000 description 1
- HIMZRZLQRICRBL-UHFFFAOYSA-N CN(C(CNC(C=1C(NC2=CC=C(C=C2)Cl)=CC=CC1)=O)C)C Chemical compound CN(C(CNC(C=1C(NC2=CC=C(C=C2)Cl)=CC=CC1)=O)C)C HIMZRZLQRICRBL-UHFFFAOYSA-N 0.000 description 1
- IABZIXWNEKXXRX-UHFFFAOYSA-N CN(CCCNC(C=1C(NC2=C(C=CC=C2)C)=CC=CC1)=O)C Chemical compound CN(CCCNC(C=1C(NC2=C(C=CC=C2)C)=CC=CC1)=O)C IABZIXWNEKXXRX-UHFFFAOYSA-N 0.000 description 1
- XVSONGYGGHBBCG-UHFFFAOYSA-N CN(CCCNC(C=1C(NC2=C(C=CC=C2)Cl)=CC=CC1)=O)C Chemical compound CN(CCCNC(C=1C(NC2=C(C=CC=C2)Cl)=CC=CC1)=O)C XVSONGYGGHBBCG-UHFFFAOYSA-N 0.000 description 1
- JSQFQLMEQHSSPY-UHFFFAOYSA-N CN(CCCNC(C=1C(NC2=CC(=CC=C2)C)=CC=CC1)=O)C Chemical compound CN(CCCNC(C=1C(NC2=CC(=CC=C2)C)=CC=CC1)=O)C JSQFQLMEQHSSPY-UHFFFAOYSA-N 0.000 description 1
- SAFAPQHEAOFDBX-UHFFFAOYSA-N CN(CCCNC(C=1C(NC2=CC(=CC=C2)Cl)=CC=CC1)=O)C Chemical compound CN(CCCNC(C=1C(NC2=CC(=CC=C2)Cl)=CC=CC1)=O)C SAFAPQHEAOFDBX-UHFFFAOYSA-N 0.000 description 1
- CKOGAVOIQSCSBR-UHFFFAOYSA-N CN(CCNC(C=1C(NC2=C(C=CC=C2)Cl)=CC=CC1)=O)C Chemical compound CN(CCNC(C=1C(NC2=C(C=CC=C2)Cl)=CC=CC1)=O)C CKOGAVOIQSCSBR-UHFFFAOYSA-N 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- XTLWKZXACGMAEE-UHFFFAOYSA-N N-[2-(dimethylamino)ethyl]-2-(2,3-dimethylanilino)benzamide Chemical compound CN(CCNC(C=1C(NC2=C(C(=CC=C2)C)C)=CC=CC1)=O)C XTLWKZXACGMAEE-UHFFFAOYSA-N 0.000 description 1
- XEGMHSXUUGQSRE-UHFFFAOYSA-N N-[2-(dimethylamino)propyl]-2-(2,3-dimethylanilino)benzamide Chemical compound CN(C(CNC(C=1C(NC2=C(C(=CC=C2)C)C)=CC=CC1)=O)C)C XEGMHSXUUGQSRE-UHFFFAOYSA-N 0.000 description 1
- HDHNBQUHDLEKQJ-UHFFFAOYSA-N N-[2-(dimethylamino)propyl]-2-(3-methylanilino)benzamide Chemical compound CN(C(CNC(C=1C(NC2=CC(=CC=C2)C)=CC=CC1)=O)C)C HDHNBQUHDLEKQJ-UHFFFAOYSA-N 0.000 description 1
- BNBKHRDAXHJFED-UHFFFAOYSA-N N-[3-(diethylamino)propyl]-2-(2,3-dimethylanilino)benzamide Chemical compound C(C)N(CCCNC(C=1C(NC2=C(C(=CC=C2)C)C)=CC=CC1)=O)CC BNBKHRDAXHJFED-UHFFFAOYSA-N 0.000 description 1
- VJGBPXHNNKNBJB-UHFFFAOYSA-N N-[3-(diethylamino)propyl]-2-(3-methylanilino)benzamide Chemical compound C(C)N(CCCNC(C=1C(NC2=CC(=CC=C2)C)=CC=CC1)=O)CC VJGBPXHNNKNBJB-UHFFFAOYSA-N 0.000 description 1
- DCTDFFWFCRRWOR-UHFFFAOYSA-N N-[3-(diethylamino)propyl]-2-[3-(trifluoromethyl)anilino]benzamide Chemical compound C(C)N(CCCNC(C=1C(NC2=CC(=CC=C2)C(F)(F)F)=CC=CC1)=O)CC DCTDFFWFCRRWOR-UHFFFAOYSA-N 0.000 description 1
- 206010038743 Restlessness Diseases 0.000 description 1
- 229960000212 aminophenazone Drugs 0.000 description 1
- 230000036592 analgesia Effects 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000010411 cooking Methods 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical class C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 1
- XPXMKIXDFWLRAA-UHFFFAOYSA-N hydrazinide Chemical compound [NH-]N XPXMKIXDFWLRAA-UHFFFAOYSA-N 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- HYYBABOKPJLUIN-UHFFFAOYSA-N mefenamic acid Chemical compound CC1=CC=CC(NC=2C(=CC=CC=2)C(O)=O)=C1C HYYBABOKPJLUIN-UHFFFAOYSA-N 0.000 description 1
- CQDGTJPVBWZJAZ-UHFFFAOYSA-N monoethyl carbonate Chemical compound CCOC(O)=O CQDGTJPVBWZJAZ-UHFFFAOYSA-N 0.000 description 1
- YBEFXFBAXWUBNQ-UHFFFAOYSA-N n-methylmethanamine;propan-1-amine Chemical compound CNC.CCCN YBEFXFBAXWUBNQ-UHFFFAOYSA-N 0.000 description 1
- 230000003533 narcotic effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
- C07D265/12—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems
- C07D265/14—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D265/24—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with hetero atoms directly attached in positions 2 and 4
- C07D265/26—Two oxygen atoms, e.g. isatoic anhydride
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DK342267A DK121236B (da) | 1967-07-03 | 1967-07-03 | Analogifremgangsmåde til fremstilling af terapeutisk aktive, basisk substituerede amider af N-substituerede antranilsyrer, eller syreadditionssalte deraf. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO121213B true NO121213B (de) | 1971-02-01 |
Family
ID=8122684
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO265268A NO121213B (de) | 1967-07-03 | 1968-07-02 |
Country Status (13)
| Country | Link |
|---|---|
| BE (1) | BE717543A (de) |
| BR (1) | BR6800332D0 (de) |
| CA (1) | CA921051A (de) |
| CH (1) | CH512436A (de) |
| DK (1) | DK121236B (de) |
| ES (1) | ES355674A1 (de) |
| FI (1) | FI49024C (de) |
| FR (1) | FR1584334A (de) |
| GB (1) | GB1165300A (de) |
| IE (1) | IE32158B1 (de) |
| NL (1) | NL163503C (de) |
| NO (1) | NO121213B (de) |
| SE (1) | SE363504B (de) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20090221703A1 (en) | 2006-07-09 | 2009-09-03 | Chongxi Yu | High penetration composition and uses thereof |
| US20090238763A1 (en) | 2006-07-09 | 2009-09-24 | Chongxi Yu | High penetration compositions and uses thereof |
| ES2694685T3 (es) * | 2006-09-03 | 2018-12-26 | Techfields Biochem Co. Ltd | Profármacos solubles en agua cargados positivamente de ácidos n-arilantranílicos con muy rápida velocidad de penetración en la piel |
| JP2010529101A (ja) * | 2007-06-04 | 2010-08-26 | テックフィールズ インコーポレイテッド | 非常に速い皮膚及び膜浸透速度を有するｎｓａｉａプロドラッグ及びその新規医薬使用 |
| MX362949B (es) | 2008-12-04 | 2019-02-27 | Yu Chongxi | Composiciones de alta penetracion y sus aplicaciones. |
| CN107929743B (zh) | 2012-01-18 | 2023-09-01 | 苏州泰飞尔医药有限公司 | 治疗肺部疾病的高穿透力前药组合物和医药组合物 |
| JP6153264B2 (ja) * | 2015-01-05 | 2017-06-28 | テックフィールズ インコーポレイテッド | 非常に速い皮膚及び膜浸透速度を有するｎｓａｉａプロドラッグ及びその新規医薬使用 |
-
1967
- 1967-07-03 DK DK342267A patent/DK121236B/da not_active IP Right Cessation
-
1968
- 1968-06-24 IE IE74768A patent/IE32158B1/xx unknown
- 1968-06-25 GB GB3033568A patent/GB1165300A/en not_active Expired
- 1968-07-02 NO NO265268A patent/NO121213B/no unknown
- 1968-07-02 CH CH989768A patent/CH512436A/de not_active IP Right Cessation
- 1968-07-02 NL NL6809321A patent/NL163503C/xx active
- 1968-07-02 FR FR1584334D patent/FR1584334A/fr not_active Expired
- 1968-07-02 ES ES355674A patent/ES355674A1/es not_active Expired
- 1968-07-02 BR BR20033268A patent/BR6800332D0/pt unknown
- 1968-07-03 FI FI191768A patent/FI49024C/fi active
- 1968-07-03 BE BE717543D patent/BE717543A/xx unknown
- 1968-07-03 SE SE918268A patent/SE363504B/xx unknown
- 1968-07-03 CA CA024135A patent/CA921051A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FI49024B (de) | 1974-12-02 |
| IE32158B1 (en) | 1973-05-02 |
| DE1768818A1 (de) | 1971-12-30 |
| FR1584334A (de) | 1969-12-19 |
| ES355674A1 (es) | 1970-01-01 |
| FI49024C (fi) | 1975-03-10 |
| NL163503C (nl) | 1980-09-15 |
| NL6809321A (de) | 1969-01-07 |
| IE32158L (en) | 1969-01-03 |
| BR6800332D0 (pt) | 1973-02-13 |
| GB1165300A (en) | 1969-09-24 |
| BE717543A (de) | 1968-12-16 |
| DK121236B (da) | 1971-09-27 |
| DE1768818B2 (de) | 1977-05-05 |
| CH512436A (de) | 1971-09-15 |
| NL163503B (nl) | 1980-04-15 |
| CA921051A (en) | 1973-02-13 |
| SE363504B (de) | 1974-01-21 |
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