NO840292L - Pyrrol-2-acetylaminosyre-derivater. - Google Patents
Pyrrol-2-acetylaminosyre-derivater.Info
- Publication number
- NO840292L NO840292L NO840292A NO840292A NO840292L NO 840292 L NO840292 L NO 840292L NO 840292 A NO840292 A NO 840292A NO 840292 A NO840292 A NO 840292A NO 840292 L NO840292 L NO 840292L
- Authority
- NO
- Norway
- Prior art keywords
- pyrrol
- methyl
- acetyl
- dimethyl
- mol
- Prior art date
Links
- -1 Amide ester compound Chemical class 0.000 claims description 37
- 150000001875 compounds Chemical class 0.000 claims description 28
- 239000002253 acid Substances 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 150000004820 halides Chemical group 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- 101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 claims 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 2
- SEISQYMYXCDENP-AWEZNQCLSA-N (2s)-2-[[2-[5-(4-chlorobenzoyl)-1,4-dimethylpyrrol-2-yl]acetyl]amino]butanedioic acid Chemical group C1=C(CC(=O)N[C@@H](CC(O)=O)C(O)=O)N(C)C(C(=O)C=2C=CC(Cl)=CC=2)=C1C SEISQYMYXCDENP-AWEZNQCLSA-N 0.000 claims 1
- HDOORRVLRJDOKF-UHFFFAOYSA-M sodium;2-[[2-[1-methyl-5-(4-methylbenzoyl)pyrrol-2-yl]acetyl]amino]acetate Chemical group [Na+].C1=CC(C)=CC=C1C(=O)C1=CC=C(CC(=O)NCC([O-])=O)N1C HDOORRVLRJDOKF-UHFFFAOYSA-M 0.000 claims 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 42
- 239000000243 solution Substances 0.000 description 33
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
- 229940024606 amino acid Drugs 0.000 description 22
- 239000007787 solid Substances 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- 229910001868 water Inorganic materials 0.000 description 21
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
- 235000001014 amino acid Nutrition 0.000 description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 239000000203 mixture Substances 0.000 description 17
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
- 230000008018 melting Effects 0.000 description 16
- 238000002844 melting Methods 0.000 description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 14
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
- UPSPUYADGBWSHF-UHFFFAOYSA-N tolmetin Chemical compound C1=CC(C)=CC=C1C(=O)C1=CC=C(CC(O)=O)N1C UPSPUYADGBWSHF-UHFFFAOYSA-N 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 11
- UIIMBOGNXHQVGW-UHFFFAOYSA-M sodium bicarbonate Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 11
- 229960001017 tolmetin Drugs 0.000 description 11
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 10
- 238000010992 reflux Methods 0.000 description 10
- ZXVNMYWKKDOREA-UHFFFAOYSA-N zomepirac Chemical compound C1=C(CC(O)=O)N(C)C(C(=O)C=2C=CC(Cl)=CC=2)=C1C ZXVNMYWKKDOREA-UHFFFAOYSA-N 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- 230000003110 anti-inflammatory effect Effects 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 7
- 229940079593 drug Drugs 0.000 description 7
- 239000003814 drug Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- 229960000583 acetic acid Drugs 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- COQRGFWWJBEXRC-UHFFFAOYSA-N hydron;methyl 2-aminoacetate;chloride Chemical compound Cl.COC(=O)CN COQRGFWWJBEXRC-UHFFFAOYSA-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
- 235000017557 sodium bicarbonate Nutrition 0.000 description 6
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
- ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 description 5
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 5
- 150000001413 amino acids Chemical class 0.000 description 5
- 239000000010 aprotic solvent Substances 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 4
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
- 208000025865 Ulcer Diseases 0.000 description 4
- 125000004442 acylamino group Chemical group 0.000 description 4
- 238000005917 acylation reaction Methods 0.000 description 4
- 230000000202 analgesic effect Effects 0.000 description 4
- 150000008064 anhydrides Chemical class 0.000 description 4
- ILZINBBOCYJKKV-UHFFFAOYSA-N cyanomethyl 2-[1-methyl-5-(4-methylbenzoyl)pyrrol-2-yl]acetate Chemical compound CN1C(=CC=C1C(C1=CC=C(C=C1)C)=O)CC(=O)OCC#N ILZINBBOCYJKKV-UHFFFAOYSA-N 0.000 description 4
- 230000002496 gastric effect Effects 0.000 description 4
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 description 4
- 235000004554 glutamine Nutrition 0.000 description 4
- DWKPPFQULDPWHX-VKHMYHEASA-N l-alanyl ester Chemical compound COC(=O)[C@H](C)N DWKPPFQULDPWHX-VKHMYHEASA-N 0.000 description 4
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 4
- 230000036269 ulceration Effects 0.000 description 4
- 229960003414 zomepirac Drugs 0.000 description 4
- RENMDAKOXSCIGH-UHFFFAOYSA-N Chloroacetonitrile Chemical compound ClCC#N RENMDAKOXSCIGH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000004471 Glycine Substances 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 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
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000010933 acylation Effects 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 3
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 3
- ZZVSEQRZMCYSEB-UHFFFAOYSA-N methyl 2-[[2-[1-methyl-5-(4-methylbenzoyl)pyrrol-2-yl]acetyl]amino]acetate Chemical compound CN1C(CC(=O)NCC(=O)OC)=CC=C1C(=O)C1=CC=C(C)C=C1 ZZVSEQRZMCYSEB-UHFFFAOYSA-N 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 235000011181 potassium carbonates Nutrition 0.000 description 3
- 150000003180 prostaglandins Chemical class 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- 231100001274 therapeutic index Toxicity 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- ZRQZEGGYLWWKEW-UHFFFAOYSA-N 2-[5-(4-chlorobenzoyl)-1,4-dimethylpyrrol-2-yl]acetyl chloride Chemical compound C1=C(CC(Cl)=O)N(C)C(C(=O)C=2C=CC(Cl)=CC=2)=C1C ZRQZEGGYLWWKEW-UHFFFAOYSA-N 0.000 description 2
- IYNXNYQOVKPFMM-UHFFFAOYSA-N 2-[[2-[1-methyl-5-(4-methylbenzoyl)pyrrol-2-yl]acetyl]amino]acetic acid Chemical compound C1=CC(C)=CC=C1C(=O)C1=CC=C(CC(=O)NCC(O)=O)N1C IYNXNYQOVKPFMM-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 206010053155 Epigastric discomfort Diseases 0.000 description 2
- 208000009386 Experimental Arthritis Diseases 0.000 description 2
- 206010070840 Gastrointestinal tract irritation Diseases 0.000 description 2
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 2
- YEJSPQZHMWGIGP-YFKPBYRVSA-N L-glutamic acid, dimethyl ester Chemical compound COC(=O)CC[C@H](N)C(=O)OC YEJSPQZHMWGIGP-YFKPBYRVSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 241000186359 Mycobacterium Species 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- MFUPLHQOVIUESQ-JEDNCBNOSA-N [(2s)-1,5-dimethoxy-1,5-dioxopentan-2-yl]azanium;chloride Chemical compound Cl.COC(=O)CC[C@H](N)C(=O)OC MFUPLHQOVIUESQ-JEDNCBNOSA-N 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 150000003862 amino acid derivatives Chemical class 0.000 description 2
- 239000007900 aqueous suspension Substances 0.000 description 2
- 239000002152 aqueous-organic solution Substances 0.000 description 2
- 230000002917 arthritic effect Effects 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- 159000000007 calcium salts Chemical class 0.000 description 2
- 235000011089 carbon dioxide Nutrition 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- XTTKNGNSGIHDGS-UHFFFAOYSA-N cyanomethyl 2-[5-(4-chlorobenzoyl)-1,4-dimethylpyrrol-2-yl]acetate Chemical compound C1=C(CC(=O)OCC#N)N(C)C(C(=O)C=2C=CC(Cl)=CC=2)=C1C XTTKNGNSGIHDGS-UHFFFAOYSA-N 0.000 description 2
- 238000006264 debenzylation reaction Methods 0.000 description 2
- 125000004185 ester group Chemical group 0.000 description 2
- 210000002683 foot Anatomy 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 229960002989 glutamic acid Drugs 0.000 description 2
- 235000013922 glutamic acid Nutrition 0.000 description 2
- 239000004220 glutamic acid Substances 0.000 description 2
- 210000000548 hind-foot Anatomy 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 238000011694 lewis rat Methods 0.000 description 2
- 229940059904 light mineral oil Drugs 0.000 description 2
- 229920000609 methyl cellulose Polymers 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- 239000001923 methylcellulose Substances 0.000 description 2
- 125000004372 methylthioethyl group Chemical group [H]C([H])([H])SC([H])([H])C([H])([H])* 0.000 description 2
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 description 2
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 230000001562 ulcerogenic effect Effects 0.000 description 2
- BROKTQXVZXUGEN-LMOVPXPDSA-N (2S)-6-amino-2-[[2-[5-(4-chlorobenzoyl)-1,4-dimethylpyrrol-2-yl]acetyl]amino]hexanoic acid hydrate Chemical compound O.C1=C(CC(=O)N[C@@H](CCCCN)C(O)=O)N(C)C(C(=O)C=2C=CC(Cl)=CC=2)=C1C BROKTQXVZXUGEN-LMOVPXPDSA-N 0.000 description 1
- RLNCYOJMVOUCJR-AWEZNQCLSA-N (2s)-2-[[2-[1-methyl-5-(4-methylbenzoyl)pyrrol-2-yl]acetyl]amino]butanedioic acid Chemical compound C1=CC(C)=CC=C1C(=O)C1=CC=C(CC(=O)N[C@@H](CC(O)=O)C(O)=O)N1C RLNCYOJMVOUCJR-AWEZNQCLSA-N 0.000 description 1
- QOZTVGDPWCHJLC-KRWDZBQOSA-N (2s)-2-[[2-[5-(4-chlorobenzoyl)-1,4-dimethylpyrrol-2-yl]acetyl]amino]-3-methylbutanoic acid Chemical compound CN1C(CC(=O)N[C@@H](C(C)C)C(O)=O)=CC(C)=C1C(=O)C1=CC=C(Cl)C=C1 QOZTVGDPWCHJLC-KRWDZBQOSA-N 0.000 description 1
- MTDASQIJQLNHLZ-KRWDZBQOSA-N (2s)-2-[[2-[5-(4-chlorobenzoyl)-1,4-dimethylpyrrol-2-yl]acetyl]amino]-4-methylpentanoic acid Chemical compound CN1C(CC(=O)N[C@@H](CC(C)C)C(O)=O)=CC(C)=C1C(=O)C1=CC=C(Cl)C=C1 MTDASQIJQLNHLZ-KRWDZBQOSA-N 0.000 description 1
- MWCZYRNVNZPXPG-SFHVURJKSA-N (2s)-3-methyl-2-[[2-[1-methyl-5-(4-methylbenzoyl)pyrrol-2-yl]acetyl]amino]butanoic acid Chemical compound CN1C(CC(=O)N[C@@H](C(C)C)C(O)=O)=CC=C1C(=O)C1=CC=C(C)C=C1 MWCZYRNVNZPXPG-SFHVURJKSA-N 0.000 description 1
- JVTVRJCLUQQRJS-KRWDZBQOSA-N (2s)-4-methyl-2-[[2-[1-methyl-5-(4-methylbenzoyl)pyrrol-2-yl]acetyl]amino]pentanoic acid Chemical compound CN1C(CC(=O)N[C@@H](CC(C)C)C(O)=O)=CC=C1C(=O)C1=CC=C(C)C=C1 JVTVRJCLUQQRJS-KRWDZBQOSA-N 0.000 description 1
- RIJHSIIWIHRHCZ-SGTLLEGYSA-N (2s,3s)-2-[[2-[5-(4-chlorobenzoyl)-1,4-dimethylpyrrol-2-yl]acetyl]amino]-3-methylpentanoic acid Chemical compound CN1C(CC(=O)N[C@@H]([C@@H](C)CC)C(O)=O)=CC(C)=C1C(=O)C1=CC=C(Cl)C=C1 RIJHSIIWIHRHCZ-SGTLLEGYSA-N 0.000 description 1
- XVQMQHCOBNZYGG-LIRRHRJNSA-N (2s,3s)-3-methyl-2-[[2-[1-methyl-5-(4-methylbenzoyl)pyrrol-2-yl]acetyl]amino]pentanoic acid Chemical compound CN1C(CC(=O)N[C@@H]([C@@H](C)CC)C(O)=O)=CC=C1C(=O)C1=CC=C(C)C=C1 XVQMQHCOBNZYGG-LIRRHRJNSA-N 0.000 description 1
- YHXZADSGRNQVOT-UHFFFAOYSA-N 2-[1-methyl-5-(4-methylbenzoyl)pyrrol-2-yl]acetyl chloride Chemical compound C1=CC(C)=CC=C1C(=O)C1=CC=C(CC(Cl)=O)N1C YHXZADSGRNQVOT-UHFFFAOYSA-N 0.000 description 1
- PXIILGMREWTUMN-UHFFFAOYSA-N 2-[1-methyl-5-[(4-methylphenyl)methyl]pyrrol-2-yl]acetyl chloride Chemical compound C1=CC(C)=CC=C1CC1=CC=C(CC(Cl)=O)N1C PXIILGMREWTUMN-UHFFFAOYSA-N 0.000 description 1
- YOETUEMZNOLGDB-UHFFFAOYSA-N 2-methylpropyl carbonochloridate Chemical compound CC(C)COC(Cl)=O YOETUEMZNOLGDB-UHFFFAOYSA-N 0.000 description 1
- DEXFNLNNUZKHNO-UHFFFAOYSA-N 6-[3-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperidin-1-yl]-3-oxopropyl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1CCN(CC1)C(CCC1=CC2=C(NC(O2)=O)C=C1)=O DEXFNLNNUZKHNO-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- DHMQDGOQFOQNFH-UHFFFAOYSA-M Aminoacetate Chemical compound NCC([O-])=O DHMQDGOQFOQNFH-UHFFFAOYSA-M 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- GSNUFIFRDBKVIE-UHFFFAOYSA-N DMF Natural products CC1=CC=C(C)O1 GSNUFIFRDBKVIE-UHFFFAOYSA-N 0.000 description 1
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 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
- 229930182816 L-glutamine Natural products 0.000 description 1
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 1
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 238000003436 Schotten-Baumann reaction Methods 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- ZEHGKSPCAMLJDC-UHFFFAOYSA-M acetylcholine bromide Chemical compound [Br-].CC(=O)OCC[N+](C)(C)C ZEHGKSPCAMLJDC-UHFFFAOYSA-M 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 235000004279 alanine Nutrition 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 235000003704 aspartic acid Nutrition 0.000 description 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 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
- 230000000903 blocking effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- OZDCHRUHPOMNTD-UQKRIMTDSA-L calcium;(2s)-2-[[2-[1-methyl-5-(4-methylbenzoyl)pyrrol-2-yl]acetyl]amino]butanedioate Chemical compound [Ca+2].C1=CC(C)=CC=C1C(=O)C1=CC=C(CC(=O)N[C@@H](CC([O-])=O)C([O-])=O)N1C OZDCHRUHPOMNTD-UQKRIMTDSA-L 0.000 description 1
- FHLCLPAFRLRPHY-WUBQCMAVSA-L calcium;(2s)-2-[[2-[5-(4-chlorobenzoyl)-1,4-dimethylpyrrol-2-yl]acetyl]amino]-4-methylsulfanylbutanoate Chemical compound [Ca+2].CN1C(CC(=O)N[C@@H](CCSC)C([O-])=O)=CC(C)=C1C(=O)C1=CC=C(Cl)C=C1.CN1C(CC(=O)N[C@@H](CCSC)C([O-])=O)=CC(C)=C1C(=O)C1=CC=C(Cl)C=C1 FHLCLPAFRLRPHY-WUBQCMAVSA-L 0.000 description 1
- 229960004424 carbon dioxide Drugs 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000005341 cation exchange Methods 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- SKCNIGRBPJIUBQ-UHFFFAOYSA-N chloroform;ethyl acetate Chemical compound ClC(Cl)Cl.CCOC(C)=O SKCNIGRBPJIUBQ-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- DNIBDFSODHFJAF-NDEPHWFRSA-N dibenzyl (2s)-2-[[2-[1-methyl-5-(4-methylbenzoyl)pyrrol-2-yl]acetyl]amino]butanedioate Chemical compound C1=CC(C)=CC=C1C(=O)C(N1C)=CC=C1CC(=O)N[C@H](C(=O)OCC=1C=CC=CC=1)CC(=O)OCC1=CC=CC=C1 DNIBDFSODHFJAF-NDEPHWFRSA-N 0.000 description 1
- MZCGVKOTLAYNEA-KRWDZBQOSA-N dimethyl (2s)-2-[[2-[1-methyl-5-(4-methylbenzoyl)pyrrol-2-yl]acetyl]amino]pentanedioate Chemical compound CN1C(CC(=O)N[C@@H](CCC(=O)OC)C(=O)OC)=CC=C1C(=O)C1=CC=C(C)C=C1 MZCGVKOTLAYNEA-KRWDZBQOSA-N 0.000 description 1
- CDBUDOCXUIULIL-KRWDZBQOSA-N dimethyl (2s)-2-[[2-[5-(4-chlorobenzoyl)-1,4-dimethylpyrrol-2-yl]acetyl]amino]pentanedioate Chemical compound CN1C(CC(=O)N[C@@H](CCC(=O)OC)C(=O)OC)=CC(C)=C1C(=O)C1=CC=C(Cl)C=C1 CDBUDOCXUIULIL-KRWDZBQOSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- MSYBLBLAMDYKKZ-UHFFFAOYSA-N hydron;pyridine-3-carbonyl chloride;chloride Chemical compound Cl.ClC(=O)C1=CC=CN=C1 MSYBLBLAMDYKKZ-UHFFFAOYSA-N 0.000 description 1
- 239000000893 inhibin Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- ZPNFWUPYTFPOJU-LPYSRVMUSA-N iniprol Chemical compound C([C@H]1C(=O)NCC(=O)NCC(=O)N[C@H]2CSSC[C@H]3C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@H](C(N[C@H](C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=4C=CC(O)=CC=4)C(=O)N[C@@H](CC=4C=CC=CC=4)C(=O)N[C@@H](CC=4C=CC(O)=CC=4)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](C)C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CSSC[C@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C)NC(=O)[C@H](CO)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CC=4C=CC=CC=4)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CCCCN)NC(=O)[C@H](C)NC(=O)[C@H](CCCNC(N)=N)NC2=O)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CSSC[C@H](NC(=O)[C@H](CC=2C=CC=CC=2)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H]2N(CCC2)C(=O)[C@@H](N)CCCNC(N)=N)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)N2[C@@H](CCC2)C(=O)N2[C@@H](CCC2)C(=O)N[C@@H](CC=2C=CC(O)=CC=2)C(=O)N[C@@H]([C@@H](C)O)C(=O)NCC(=O)N2[C@@H](CCC2)C(=O)N3)C(=O)NCC(=O)NCC(=O)N[C@@H](C)C(O)=O)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@H](C(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@H](C(=O)N1)C(C)C)[C@@H](C)O)[C@@H](C)CC)=O)[C@@H](C)CC)C1=CC=C(O)C=C1 ZPNFWUPYTFPOJU-LPYSRVMUSA-N 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 239000000543 intermediate Substances 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
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 235000018977 lysine Nutrition 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229930182817 methionine Natural products 0.000 description 1
- YJELSSKBYZBGLL-LBPRGKRZSA-N methyl (2s)-2-[[2-[5-(4-chlorobenzoyl)-1,4-dimethylpyrrol-2-yl]acetyl]amino]propanoate Chemical compound CN1C(CC(=O)N[C@@H](C)C(=O)OC)=CC(C)=C1C(=O)C1=CC=C(Cl)C=C1 YJELSSKBYZBGLL-LBPRGKRZSA-N 0.000 description 1
- WVAZCUWAJLUWNP-UHFFFAOYSA-N methyl 2-[[2-[5-(4-chlorobenzoyl)-1,4-dimethylpyrrol-2-yl]acetyl]amino]acetate Chemical compound CN1C(CC(=O)NCC(=O)OC)=CC(C)=C1C(=O)C1=CC=C(Cl)C=C1 WVAZCUWAJLUWNP-UHFFFAOYSA-N 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- RDSJNYZPSNHNRF-LMOVPXPDSA-M sodium;(2s)-6-amino-2-[[2-[1-methyl-5-(4-methylbenzoyl)pyrrol-2-yl]acetyl]amino]hexanoate Chemical compound [Na+].C1=CC(C)=CC=C1C(=O)C1=CC=C(CC(=O)N[C@@H](CCCCN)C([O-])=O)N1C RDSJNYZPSNHNRF-LMOVPXPDSA-M 0.000 description 1
- SEEXPXUCHVGZGU-UHFFFAOYSA-M sodium;2-[5-(4-chlorobenzoyl)-1,4-dimethylpyrrol-2-yl]acetate Chemical compound [Na+].C1=C(CC([O-])=O)N(C)C(C(=O)C=2C=CC(Cl)=CC=2)=C1C SEEXPXUCHVGZGU-UHFFFAOYSA-M 0.000 description 1
- CTXPSZRDTDCQJJ-UHFFFAOYSA-M sodium;2-[[2-[5-(4-chlorobenzoyl)-1,4-dimethylpyrrol-2-yl]acetyl]amino]acetate Chemical compound [Na+].C1=C(CC(=O)NCC([O-])=O)N(C)C(C(=O)C=2C=CC(Cl)=CC=2)=C1C CTXPSZRDTDCQJJ-UHFFFAOYSA-M 0.000 description 1
- WZWGGYFEOBVNLA-UHFFFAOYSA-N sodium;dihydrate Chemical compound O.O.[Na] WZWGGYFEOBVNLA-UHFFFAOYSA-N 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- QGUALMNFRILWRA-UHFFFAOYSA-M tolmetin sodium Chemical compound [Na+].C1=CC(C)=CC=C1C(=O)C1=CC=C(CC([O-])=O)N1C QGUALMNFRILWRA-UHFFFAOYSA-M 0.000 description 1
- 229960002044 tolmetin sodium Drugs 0.000 description 1
- UPSPUYADGBWSHF-UHFFFAOYSA-M tolmetin(1-) Chemical compound C1=CC(C)=CC=C1C(=O)C1=CC=C(CC([O-])=O)N1C UPSPUYADGBWSHF-UHFFFAOYSA-M 0.000 description 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 1
- 229960000281 trometamol Drugs 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 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
- C07D207/30—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 two double bonds between ring members or between ring members and non-ring members
- C07D207/34—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 two 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyrrole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US46104783A | 1983-01-26 | 1983-01-26 | |
| US06/461,055 US4585784A (en) | 1983-01-26 | 1983-01-26 | Pyrrole-2-acetylamino acid derivative compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO840292L true NO840292L (no) | 1984-07-27 |
Family
ID=27039899
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO840292A NO840292L (no) | 1983-01-26 | 1984-01-25 | Pyrrol-2-acetylaminosyre-derivater. |
Country Status (12)
| Country | Link |
|---|---|
| EP (1) | EP0115424B1 (xx) |
| AU (1) | AU556810B2 (xx) |
| DE (1) | DE3467164D1 (xx) |
| DK (1) | DK33284A (xx) |
| ES (2) | ES8504704A1 (xx) |
| FI (1) | FI840299A (xx) |
| GB (1) | GB2134111B (xx) |
| HU (1) | HU195232B (xx) |
| IE (1) | IE56608B1 (xx) |
| NO (1) | NO840292L (xx) |
| NZ (1) | NZ206818A (xx) |
| YU (1) | YU251283A (xx) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1210673B (it) * | 1982-02-26 | 1989-09-20 | Medosan Ind Biochimi | Antinfiammatoria amidi pirrolacetiche ad attivita' |
| IT1197688B (it) * | 1983-07-29 | 1988-12-06 | Medosan Ind Biochimi | Attivita' antiflogistica,analgesica,antipiretica ed antiaggregante piastrinica di 1-metil-5-metilbenzoilpirrol-2-acetamido acetanilidi |
| CN103254109B (zh) * | 2013-05-31 | 2015-01-28 | 山西大学 | 一种苯甲酰基吡咯衍生物及其合成方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE338993B (xx) * | 1967-07-26 | 1971-09-27 | Mcneilab Inc | |
| US3752826A (en) * | 1970-01-26 | 1973-08-14 | Mcneilab Inc | Aroyl substituted pyrroles |
| IT1210673B (it) * | 1982-02-26 | 1989-09-20 | Medosan Ind Biochimi | Antinfiammatoria amidi pirrolacetiche ad attivita' |
-
1983
- 1983-12-27 YU YU251283A patent/YU251283A/xx unknown
-
1984
- 1984-01-11 NZ NZ20681884A patent/NZ206818A/en unknown
- 1984-01-24 ES ES529120A patent/ES8504704A1/es not_active Expired
- 1984-01-25 IE IE16784A patent/IE56608B1/xx unknown
- 1984-01-25 GB GB08401876A patent/GB2134111B/en not_active Expired
- 1984-01-25 AU AU23787/84A patent/AU556810B2/en not_active Ceased
- 1984-01-25 FI FI840299A patent/FI840299A/fi not_active Application Discontinuation
- 1984-01-25 NO NO840292A patent/NO840292L/no unknown
- 1984-01-25 EP EP19840300437 patent/EP0115424B1/en not_active Expired
- 1984-01-25 DE DE8484300437T patent/DE3467164D1/de not_active Expired
- 1984-01-25 DK DK33284A patent/DK33284A/da not_active Application Discontinuation
- 1984-01-25 HU HU31084A patent/HU195232B/hu unknown
- 1984-08-10 ES ES535101A patent/ES535101A0/es active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| IE56608B1 (en) | 1991-10-09 |
| ES529120A0 (es) | 1985-05-01 |
| GB2134111B (en) | 1986-05-29 |
| DK33284A (da) | 1984-07-27 |
| DK33284D0 (da) | 1984-01-25 |
| HU195232B (en) | 1988-04-28 |
| AU2378784A (en) | 1984-08-02 |
| AU556810B2 (en) | 1986-11-20 |
| GB2134111A (en) | 1984-08-08 |
| GB8401876D0 (en) | 1984-02-29 |
| EP0115424A1 (en) | 1984-08-08 |
| YU251283A (en) | 1986-04-30 |
| ES8506620A1 (es) | 1985-07-16 |
| FI840299A0 (fi) | 1984-01-25 |
| ES8504704A1 (es) | 1985-05-01 |
| IE840167L (en) | 1984-07-26 |
| EP0115424B1 (en) | 1987-11-04 |
| DE3467164D1 (de) | 1987-12-10 |
| NZ206818A (en) | 1986-03-14 |
| FI840299A (fi) | 1984-07-27 |
| ES535101A0 (es) | 1985-07-16 |
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