IE46506B1 - 5-(2-pyrroyl)-1,2-dihydro-3h-pyrrolo (1,2-a)pyrrole-1-carboxylic acid derivatives and process for the production thereof - Google Patents
5-(2-pyrroyl)-1,2-dihydro-3h-pyrrolo (1,2-a)pyrrole-1-carboxylic acid derivatives and process for the production thereofInfo
- Publication number
- IE46506B1 IE46506B1 IE605/78A IE60578A IE46506B1 IE 46506 B1 IE46506 B1 IE 46506B1 IE 605/78 A IE605/78 A IE 605/78A IE 60578 A IE60578 A IE 60578A IE 46506 B1 IE46506 B1 IE 46506B1
- Authority
- IE
- Ireland
- Prior art keywords
- dihydro
- pyrroyl
- pyrrole
- pyrrolo
- formula
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 37
- 230000008569 process Effects 0.000 title claims abstract description 11
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 5
- XCIRJBKDVDPXGL-UHFFFAOYSA-N 5-(1h-pyrrole-2-carbonyl)-2,3-dihydro-1h-pyrrolizine-1-carboxylic acid Chemical class OC(=O)C1CCN2C1=CC=C2C(=O)C1=CC=CN1 XCIRJBKDVDPXGL-UHFFFAOYSA-N 0.000 title claims 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 102
- 150000003839 salts Chemical class 0.000 claims abstract description 39
- 231100000252 nontoxic Toxicity 0.000 claims abstract description 32
- 230000003000 nontoxic effect Effects 0.000 claims abstract description 32
- 150000002148 esters Chemical class 0.000 claims abstract description 31
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 14
- 239000001257 hydrogen Substances 0.000 claims abstract description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 4
- 239000002253 acid Substances 0.000 claims description 74
- -1 2 - pyrroyl Chemical group 0.000 claims description 43
- 239000000203 mixture Substances 0.000 claims description 34
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 28
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 22
- 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 claims description 16
- 239000011734 sodium Substances 0.000 claims description 16
- 229910052708 sodium Inorganic materials 0.000 claims description 16
- 230000032696 parturition Effects 0.000 claims description 12
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 10
- 150000007513 acids Chemical class 0.000 claims description 10
- 239000011591 potassium Substances 0.000 claims description 10
- 229910052700 potassium Inorganic materials 0.000 claims description 10
- 206010061218 Inflammation Diseases 0.000 claims description 8
- 230000004054 inflammatory process Effects 0.000 claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims description 8
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 8
- 125000005907 alkyl ester group Chemical group 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 241000124008 Mammalia Species 0.000 claims description 6
- 208000002193 Pain Diseases 0.000 claims description 6
- 206010037660 Pyrexia Diseases 0.000 claims description 6
- 150000001408 amides Chemical class 0.000 claims description 6
- 230000027950 fever generation Effects 0.000 claims description 6
- 230000036407 pain Effects 0.000 claims description 6
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 5
- 159000000007 calcium salts Chemical class 0.000 claims description 4
- 238000009833 condensation Methods 0.000 claims description 4
- 230000005494 condensation Effects 0.000 claims description 4
- FDDQRDMHICUGQC-UHFFFAOYSA-M pyrrole-1-carboxylate Chemical compound [O-]C(=O)N1C=CC=C1 FDDQRDMHICUGQC-UHFFFAOYSA-M 0.000 claims description 4
- 150000001732 carboxylic acid derivatives Chemical group 0.000 claims 2
- 230000003301 hydrolyzing effect Effects 0.000 claims 2
- 150000007942 carboxylates Chemical class 0.000 claims 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
- FDDQRDMHICUGQC-UHFFFAOYSA-N pyrrole-1-carboxylic acid Chemical class OC(=O)N1C=CC=C1 FDDQRDMHICUGQC-UHFFFAOYSA-N 0.000 abstract description 26
- 230000000202 analgesic effect Effects 0.000 abstract description 5
- CWQMWCYKYMHGHX-UHFFFAOYSA-N 5-(1-methylpyrrole-2-carbonyl)-2,3-dihydro-1h-pyrrolizine-1-carboxylic acid Chemical compound CN1C=CC=C1C(=O)C1=CC=C2N1CCC2C(O)=O CWQMWCYKYMHGHX-UHFFFAOYSA-N 0.000 abstract description 4
- 239000000050 smooth muscle relaxant Substances 0.000 abstract description 4
- 230000003110 anti-inflammatory effect Effects 0.000 abstract description 3
- 239000002221 antipyretic Substances 0.000 abstract 1
- 229940125716 antipyretic agent Drugs 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 63
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 54
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 35
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 30
- 239000004615 ingredient Substances 0.000 description 30
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 28
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 27
- 238000006243 chemical reaction Methods 0.000 description 25
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 24
- 239000011541 reaction mixture Substances 0.000 description 21
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 20
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 20
- 239000003826 tablet Substances 0.000 description 20
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 16
- 239000008101 lactose Substances 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
- 229920002261 Corn starch Polymers 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 239000008120 corn starch Substances 0.000 description 12
- 229940099112 cornstarch Drugs 0.000 description 12
- 235000019359 magnesium stearate Nutrition 0.000 description 12
- 238000010992 reflux Methods 0.000 description 12
- 238000011282 treatment Methods 0.000 description 12
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 11
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 10
- 239000002775 capsule Substances 0.000 description 10
- 229940031098 ethanolamine Drugs 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
- 239000000741 silica gel Substances 0.000 description 9
- 229910002027 silica gel Inorganic materials 0.000 description 9
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 239000002585 base Substances 0.000 description 8
- RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 description 8
- 210000003754 fetus Anatomy 0.000 description 8
- 239000003921 oil Substances 0.000 description 8
- 230000035935 pregnancy Effects 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 7
- 239000000284 extract Substances 0.000 description 7
- 239000007903 gelatin capsule Substances 0.000 description 7
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- NMPVEAUIHMEAQP-UHFFFAOYSA-N 2-Bromoacetaldehyde Chemical compound BrCC=O NMPVEAUIHMEAQP-UHFFFAOYSA-N 0.000 description 6
- RNJOKCPFLQMDEC-UHFFFAOYSA-N 4(R),8-dimethyl-trans-2-nonenoyl-CoA Chemical compound COC(=O)CC(=O)CC(=O)OC RNJOKCPFLQMDEC-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 6
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 6
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- 241000699670 Mus sp. Species 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000012298 atmosphere Substances 0.000 description 6
- VQFAIAKCILWQPZ-UHFFFAOYSA-N bromoacetone Chemical compound CC(=O)CBr VQFAIAKCILWQPZ-UHFFFAOYSA-N 0.000 description 6
- 239000011575 calcium Substances 0.000 description 6
- 229910052791 calcium Inorganic materials 0.000 description 6
- 238000002425 crystallisation Methods 0.000 description 6
- 230000008025 crystallization Effects 0.000 description 6
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 239000011777 magnesium Substances 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 5
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 5
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 5
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 5
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 5
- 229960001231 choline Drugs 0.000 description 5
- 238000004587 chromatography analysis Methods 0.000 description 5
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 5
- 230000007062 hydrolysis Effects 0.000 description 5
- 238000006460 hydrolysis reaction Methods 0.000 description 5
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- 239000001632 sodium acetate Substances 0.000 description 5
- 235000017281 sodium acetate Nutrition 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 239000000829 suppository Substances 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 5
- 229960000281 trometamol Drugs 0.000 description 5
- MFGOZCIHXVFZBC-UHFFFAOYSA-N 1-propylpyrrole Chemical compound CCCN1C=CC=C1 MFGOZCIHXVFZBC-UHFFFAOYSA-N 0.000 description 4
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 4
- 108010010803 Gelatin Proteins 0.000 description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 4
- 229930006000 Sucrose Natural products 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 239000012300 argon atmosphere Substances 0.000 description 4
- 230000037396 body weight Effects 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 239000001110 calcium chloride Substances 0.000 description 4
- 229910001628 calcium chloride Inorganic materials 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 230000008602 contraction Effects 0.000 description 4
- 238000006114 decarboxylation reaction Methods 0.000 description 4
- 239000002552 dosage form Substances 0.000 description 4
- 239000008273 gelatin Substances 0.000 description 4
- 229920000159 gelatin Polymers 0.000 description 4
- 235000019322 gelatine Nutrition 0.000 description 4
- 235000011852 gelatine desserts Nutrition 0.000 description 4
- 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 4
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 159000000003 magnesium salts Chemical class 0.000 description 4
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 238000000197 pyrolysis Methods 0.000 description 4
- 239000011369 resultant mixture Substances 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- 239000005720 sucrose Substances 0.000 description 4
- YAPQBXQYLJRXSA-UHFFFAOYSA-N theobromine Chemical compound CN1C(=O)NC(=O)C2=C1N=CN2C YAPQBXQYLJRXSA-UHFFFAOYSA-N 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 4
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 3
- WYTWKSYIRCEQNL-UHFFFAOYSA-N 1-ethyl-n,n-dimethylpyrrole-2-carboxamide Chemical compound CCN1C=CC=C1C(=O)N(C)C WYTWKSYIRCEQNL-UHFFFAOYSA-N 0.000 description 3
- 206010000234 Abortion spontaneous Diseases 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- LPHGQDQBBGAPDZ-UHFFFAOYSA-N Isocaffeine Natural products CN1C(=O)N(C)C(=O)C2=C1N(C)C=N2 LPHGQDQBBGAPDZ-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
- 229960001948 caffeine Drugs 0.000 description 3
- VJEONQKOZGKCAK-UHFFFAOYSA-N caffeine Natural products CN1C(=O)N(C)C(=O)C2=C1C=CN2C VJEONQKOZGKCAK-UHFFFAOYSA-N 0.000 description 3
- 229910000019 calcium carbonate Inorganic materials 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000008121 dextrose Substances 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 3
- 230000002349 favourable effect Effects 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 150000007529 inorganic bases Chemical class 0.000 description 3
- 238000002955 isolation Methods 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 3
- ASPZPNMMJSPPJA-UHFFFAOYSA-N methyl 1-(2-hydroxyethyl)-2-(2-methoxy-2-oxoethyl)pyrrole-3-carboxylate Chemical compound COC(=O)CC1=C(C(=O)OC)C=CN1CCO ASPZPNMMJSPPJA-UHFFFAOYSA-N 0.000 description 3
- GNBBNKMUZPMMTA-UHFFFAOYSA-N n,n,1-trimethylpyrrole-2-carboxamide Chemical compound CN(C)C(=O)C1=CC=CN1C GNBBNKMUZPMMTA-UHFFFAOYSA-N 0.000 description 3
- MPOLEZJZBLCXPF-UHFFFAOYSA-N n,n-dimethyl-1-propylpyrrole-2-carboxamide Chemical compound CCCN1C=CC=C1C(=O)N(C)C MPOLEZJZBLCXPF-UHFFFAOYSA-N 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 3
- 239000006187 pill Substances 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- 235000009518 sodium iodide Nutrition 0.000 description 3
- 208000000995 spontaneous abortion Diseases 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 238000004809 thin layer chromatography Methods 0.000 description 3
- 238000012384 transportation and delivery Methods 0.000 description 3
- YTLYLLTVENPWFT-UPHRSURJSA-N (Z)-3-aminoacrylic acid Chemical compound N\C=C/C(O)=O YTLYLLTVENPWFT-UPHRSURJSA-N 0.000 description 2
- ICLYJLBTOGPLMC-KVVVOXFISA-N (z)-octadec-9-enoate;tris(2-hydroxyethyl)azanium Chemical compound OCCN(CCO)CCO.CCCCCCCC\C=C/CCCCCCCC(O)=O ICLYJLBTOGPLMC-KVVVOXFISA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- CCXQVBSQUQCEEO-UHFFFAOYSA-N 1-bromobutan-2-one Chemical compound CCC(=O)CBr CCXQVBSQUQCEEO-UHFFFAOYSA-N 0.000 description 2
- LHQSUIYYJLMRAV-UHFFFAOYSA-N 1-butyl-n,n-dimethylpyrrole-2-carboxamide Chemical compound CCCCN1C=CC=C1C(=O)N(C)C LHQSUIYYJLMRAV-UHFFFAOYSA-N 0.000 description 2
- IIYSNNBEZBAQCQ-UHFFFAOYSA-N 1-butylpyrrole Chemical compound CCCCN1C=CC=C1 IIYSNNBEZBAQCQ-UHFFFAOYSA-N 0.000 description 2
- MSWZFWKMSRAUBD-IVMDWMLBSA-N 2-amino-2-deoxy-D-glucopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-IVMDWMLBSA-N 0.000 description 2
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 2
- 229940013085 2-diethylaminoethanol Drugs 0.000 description 2
- XZIIFPSPUDAGJM-UHFFFAOYSA-N 6-chloro-2-n,2-n-diethylpyrimidine-2,4-diamine Chemical compound CCN(CC)C1=NC(N)=CC(Cl)=N1 XZIIFPSPUDAGJM-UHFFFAOYSA-N 0.000 description 2
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- 239000004475 Arginine Substances 0.000 description 2
- KWIUHFFTVRNATP-UHFFFAOYSA-N Betaine Natural products C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 2
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 2
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 2
- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 description 2
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 2
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 2
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 2
- 239000004472 Lysine Substances 0.000 description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- 229930195725 Mannitol Natural products 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- KWIUHFFTVRNATP-UHFFFAOYSA-O N,N,N-trimethylglycinium Chemical compound C[N+](C)(C)CC(O)=O KWIUHFFTVRNATP-UHFFFAOYSA-O 0.000 description 2
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 2
- HTLZVHNRZJPSMI-UHFFFAOYSA-N N-ethylpiperidine Chemical compound CCN1CCCCC1 HTLZVHNRZJPSMI-UHFFFAOYSA-N 0.000 description 2
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 235000011941 Tilia x europaea Nutrition 0.000 description 2
- 208000036029 Uterine contractions during pregnancy Diseases 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 2
- 150000008041 alkali metal carbonates Chemical class 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 239000000908 ammonium hydroxide Substances 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000001754 anti-pyretic effect Effects 0.000 description 2
- 239000000010 aprotic solvent Substances 0.000 description 2
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 2
- 229960003121 arginine Drugs 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 description 2
- 229960003237 betaine Drugs 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 235000010980 cellulose Nutrition 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- SPWVRYZQLGQKGK-UHFFFAOYSA-N dichloromethane;hexane Chemical compound ClCCl.CCCCCC SPWVRYZQLGQKGK-UHFFFAOYSA-N 0.000 description 2
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- UYMKPFRHYYNDTL-UHFFFAOYSA-N ethenamine Chemical compound NC=C UYMKPFRHYYNDTL-UHFFFAOYSA-N 0.000 description 2
- UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 description 2
- 229940012017 ethylenediamine Drugs 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 229960002442 glucosamine Drugs 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 235000001727 glucose Nutrition 0.000 description 2
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 2
- 229960002885 histidine Drugs 0.000 description 2
- XGIHQYAWBCFNPY-AZOCGYLKSA-N hydrabamine Chemical compound C([C@@H]12)CC3=CC(C(C)C)=CC=C3[C@@]2(C)CCC[C@@]1(C)CNCCNC[C@@]1(C)[C@@H]2CCC3=CC(C(C)C)=CC=C3[C@@]2(C)CCC1 XGIHQYAWBCFNPY-AZOCGYLKSA-N 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 230000004968 inflammatory condition Effects 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000004571 lime Substances 0.000 description 2
- 239000008297 liquid dosage form Substances 0.000 description 2
- 229960003646 lysine Drugs 0.000 description 2
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 2
- 239000001095 magnesium carbonate Substances 0.000 description 2
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 2
- 238000003760 magnetic stirring Methods 0.000 description 2
- IPJKJLXEVHOKSE-UHFFFAOYSA-L manganese dihydroxide Chemical compound [OH-].[OH-].[Mn+2] IPJKJLXEVHOKSE-UHFFFAOYSA-L 0.000 description 2
- 239000000594 mannitol Substances 0.000 description 2
- 235000010355 mannitol Nutrition 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- OKJLPZAJOCGBEJ-UHFFFAOYSA-N methyl 1-(2-hydroxyethyl)-2-(2-methoxy-2-oxoethyl)-4-methylpyrrole-3-carboxylate Chemical compound COC(=O)CC1=C(C(=O)OC)C(C)=CN1CCO OKJLPZAJOCGBEJ-UHFFFAOYSA-N 0.000 description 2
- ODYMNWICOBATCC-UHFFFAOYSA-N methyl 1-(2-hydroxyethyl)-2-(2-methoxy-2-oxoethyl)-4-propylpyrrole-3-carboxylate Chemical compound CCCC1=CN(CCO)C(CC(=O)OC)=C1C(=O)OC ODYMNWICOBATCC-UHFFFAOYSA-N 0.000 description 2
- YLLVCPMOJDVCPF-UHFFFAOYSA-N methyl 1-(2-iodoethyl)-2-(2-methoxy-2-oxoethyl)pyrrole-3-carboxylate Chemical compound COC(=O)CC1=C(C(=O)OC)C=CN1CCI YLLVCPMOJDVCPF-UHFFFAOYSA-N 0.000 description 2
- JMOGNZPGTWZITL-UHFFFAOYSA-N methyl 2-(2-methoxy-2-oxoethyl)-1-(2-methylsulfonyloxyethyl)pyrrole-3-carboxylate Chemical compound COC(=O)CC1=C(C(=O)OC)C=CN1CCOS(C)(=O)=O JMOGNZPGTWZITL-UHFFFAOYSA-N 0.000 description 2
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 2
- 230000004118 muscle contraction Effects 0.000 description 2
- 210000000754 myometrium Anatomy 0.000 description 2
- VZRWJMZZHDOBIO-UHFFFAOYSA-N n,n-dimethyl-1h-pyrrole-2-carboxamide Chemical compound CN(C)C(=O)C1=CC=CN1 VZRWJMZZHDOBIO-UHFFFAOYSA-N 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- GEVPUGOOGXGPIO-UHFFFAOYSA-N oxalic acid;dihydrate Chemical compound O.O.OC(=O)C(O)=O GEVPUGOOGXGPIO-UHFFFAOYSA-N 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- 239000006179 pH buffering agent Substances 0.000 description 2
- 239000008177 pharmaceutical agent Substances 0.000 description 2
- 229920001515 polyalkylene glycol Polymers 0.000 description 2
- 229920000768 polyamine Polymers 0.000 description 2
- 229920001451 polypropylene glycol Polymers 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 2
- 229960004919 procaine Drugs 0.000 description 2
- 230000002035 prolonged effect Effects 0.000 description 2
- 150000003212 purines Chemical class 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 2
- 239000008299 semisolid dosage form Substances 0.000 description 2
- 229960004249 sodium acetate Drugs 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000007909 solid dosage form Substances 0.000 description 2
- 229940035044 sorbitan monolaurate Drugs 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 235000012222 talc Nutrition 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 229960004559 theobromine Drugs 0.000 description 2
- 229940117013 triethanolamine oleate Drugs 0.000 description 2
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 2
- 239000003981 vehicle Substances 0.000 description 2
- 238000009736 wetting Methods 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- XHHPPESHFGNBLU-UHFFFAOYSA-N 1-(2-iodoethyl)pyrrole Chemical compound ICCN1C=CC=C1 XHHPPESHFGNBLU-UHFFFAOYSA-N 0.000 description 1
- KDYMOUGNHJDZKT-UHFFFAOYSA-N 1-butylpyrrole-2-carboxylic acid Chemical compound CCCCN1C=CC=C1C(O)=O KDYMOUGNHJDZKT-UHFFFAOYSA-N 0.000 description 1
- BZWJDKJBAVXCMH-UHFFFAOYSA-N 1-diazopropane Chemical compound CCC=[N+]=[N-] BZWJDKJBAVXCMH-UHFFFAOYSA-N 0.000 description 1
- XCOJUFQICAEQEP-UHFFFAOYSA-N 1-ethylpyrrole-2-carboxylic acid Chemical compound CCN1C=CC=C1C(O)=O XCOJUFQICAEQEP-UHFFFAOYSA-N 0.000 description 1
- JOYDZQJINHJNPM-UHFFFAOYSA-N 1-methylpyrrole-2-carbonyl chloride Chemical compound CN1C=CC=C1C(Cl)=O JOYDZQJINHJNPM-UHFFFAOYSA-N 0.000 description 1
- ILAOVOOZLVGAJF-UHFFFAOYSA-N 1-methylpyrrole-2-carboxylic acid Chemical compound CN1C=CC=C1C(O)=O ILAOVOOZLVGAJF-UHFFFAOYSA-N 0.000 description 1
- UZNOGUIVJCIQGE-UHFFFAOYSA-N 1-propylpyrrole-2-carboxylic acid Chemical compound CCCN1C=CC=C1C(O)=O UZNOGUIVJCIQGE-UHFFFAOYSA-N 0.000 description 1
- SFGNNBCWQOIVAZ-UHFFFAOYSA-N 1h-pyrrole-2-carbonyl chloride Chemical compound ClC(=O)C1=CC=CN1 SFGNNBCWQOIVAZ-UHFFFAOYSA-N 0.000 description 1
- BBFDGMDENAEMKF-UHFFFAOYSA-N 2,2,2-trichloro-1-(1h-pyrrol-2-yl)ethanone Chemical class ClC(Cl)(Cl)C(=O)C1=CC=CN1 BBFDGMDENAEMKF-UHFFFAOYSA-N 0.000 description 1
- MAPSJTFQCGOIJY-UHFFFAOYSA-N 2,3-dihydro-1h-pyrrolizine-1-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)CCN21 MAPSJTFQCGOIJY-UHFFFAOYSA-N 0.000 description 1
- XURFNIBMLSLITI-UHFFFAOYSA-N 2-(4-methyl-1h-pyrrol-2-yl)acetic acid Chemical compound CC1=CNC(CC(O)=O)=C1 XURFNIBMLSLITI-UHFFFAOYSA-N 0.000 description 1
- LILXDMFJXYAKMK-UHFFFAOYSA-N 2-bromo-1,1-diethoxyethane Chemical compound CCOC(CBr)OCC LILXDMFJXYAKMK-UHFFFAOYSA-N 0.000 description 1
- HGDYZULTRRRRFK-UHFFFAOYSA-N 2-bromo-2-chloroacetaldehyde Chemical compound ClC(Br)C=O HGDYZULTRRRRFK-UHFFFAOYSA-N 0.000 description 1
- QSKPIOLLBIHNAC-UHFFFAOYSA-N 2-chloro-acetaldehyde Chemical compound ClCC=O QSKPIOLLBIHNAC-UHFFFAOYSA-N 0.000 description 1
- RLQZIECDMISZHS-UHFFFAOYSA-N 2-phenylcyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C=CC(=O)C(C=2C=CC=CC=2)=C1 RLQZIECDMISZHS-UHFFFAOYSA-N 0.000 description 1
- PYYQOSHGBVYMOH-UHFFFAOYSA-N 3-methylbutyl 5-(1-methylpyrrole-2-carbonyl)-2,3-dihydro-1h-pyrrolizine-1-carboxylate Chemical compound CC(C)CCOC(=O)C1CCN2C1=CC=C2C(=O)C1=CC=CN1C PYYQOSHGBVYMOH-UHFFFAOYSA-N 0.000 description 1
- ZAWZWSRZPBRFSW-UHFFFAOYSA-N 3-methylbutyl 6-ethyl-5-(1-methylpyrrole-2-carbonyl)-2,3-dihydro-1H-pyrrolizine-1-carboxylate Chemical compound CCC=1C=C2C(C(=O)OCCC(C)C)CCN2C=1C(=O)C1=CC=CN1C ZAWZWSRZPBRFSW-UHFFFAOYSA-N 0.000 description 1
- DQRNWUZIOSDBNZ-UHFFFAOYSA-N 3-methylbutyl 6-methyl-5-(1-methylpyrrole-2-carbonyl)-2,3-dihydro-1H-pyrrolizine-1-carboxylate Chemical compound CN1C(=CC=C1)C(=O)C1=C(C=C2N1CCC2C(=O)OCCC(C)C)C DQRNWUZIOSDBNZ-UHFFFAOYSA-N 0.000 description 1
- ICPQARMBESXDTH-UHFFFAOYSA-N 3h-pyrrolizine-1-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CCN21 ICPQARMBESXDTH-UHFFFAOYSA-N 0.000 description 1
- TWMAGNOIKMVTGX-UHFFFAOYSA-N 5-(1-methylpyrrole-2-carbonyl)-2,3-dihydro-1H-pyrrolizine-1-carboxylate propan-2-ylazanium Chemical compound CC(C)[NH3+].CN1C=CC=C1C(=O)C1=CC=C2N1CCC2C([O-])=O TWMAGNOIKMVTGX-UHFFFAOYSA-N 0.000 description 1
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 1
- 208000010392 Bone Fractures Diseases 0.000 description 1
- DSRSEMZKKDRSLC-UHFFFAOYSA-N C(CC)N1C(=CC=C1)C(=O)C1=C(C=C2N1CCC2C(=O)OC(C)C)C Chemical compound C(CC)N1C(=CC=C1)C(=O)C1=C(C=C2N1CCC2C(=O)OC(C)C)C DSRSEMZKKDRSLC-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 206010010254 Concussion Diseases 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- JJLJMEJHUUYSSY-UHFFFAOYSA-L Copper hydroxide Chemical compound [OH-].[OH-].[Cu+2] JJLJMEJHUUYSSY-UHFFFAOYSA-L 0.000 description 1
- 239000005750 Copper hydroxide Substances 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 description 1
- 201000005569 Gout Diseases 0.000 description 1
- 208000034693 Laceration Diseases 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 241000699667 Mus spretus Species 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 208000006399 Premature Obstetric Labor Diseases 0.000 description 1
- 206010036595 Premature delivery Diseases 0.000 description 1
- 206010036600 Premature labour Diseases 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- DLMBVBKZFDIJFC-UHFFFAOYSA-M [K+].CCCCN1C=CC=C1C(=O)C1=C(CCC)C=C2N1CCC2C([O-])=O Chemical compound [K+].CCCCN1C=CC=C1C(=O)C1=C(CCC)C=C2N1CCC2C([O-])=O DLMBVBKZFDIJFC-UHFFFAOYSA-M 0.000 description 1
- XWLNUKHXVYBOIA-UHFFFAOYSA-M [Na+].CC=1C=C2C(C([O-])=O)CCN2C=1C(=O)C1=CC=CN1 Chemical compound [Na+].CC=1C=C2C(C([O-])=O)CCN2C=1C(=O)C1=CC=CN1 XWLNUKHXVYBOIA-UHFFFAOYSA-M 0.000 description 1
- 206010000210 abortion Diseases 0.000 description 1
- 231100000176 abortion Toxicity 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- 229960001138 acetylsalicylic acid Drugs 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 231100000460 acute oral toxicity Toxicity 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 150000001351 alkyl iodides Chemical class 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- 229910021502 aluminium hydroxide Inorganic materials 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- JPUHCPXFQIXLMW-UHFFFAOYSA-N aluminium triethoxide Chemical compound CCO[Al](OCC)OCC JPUHCPXFQIXLMW-UHFFFAOYSA-N 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 229940121363 anti-inflammatory agent Drugs 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 230000001805 anti-writhing effect Effects 0.000 description 1
- 229940127218 antiplatelet drug Drugs 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 206010003246 arthritis Diseases 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- ZLLKKNYOHPLDHH-UHFFFAOYSA-L calcium;5-(1-methylpyrrole-2-carbonyl)-2,3-dihydro-1h-pyrrolizine-1-carboxylate Chemical compound [Ca+2].CN1C=CC=C1C(=O)C1=CC=C2N1CCC2C([O-])=O.CN1C=CC=C1C(=O)C1=CC=C2N1CCC2C([O-])=O ZLLKKNYOHPLDHH-UHFFFAOYSA-L 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- XTEGARKTQYYJKE-UHFFFAOYSA-N chloric acid Chemical compound OCl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-N 0.000 description 1
- 229940005991 chloric acid Drugs 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 230000009514 concussion Effects 0.000 description 1
- 239000012059 conventional drug carrier Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 229910001956 copper hydroxide Inorganic materials 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- WLXALCKAKGDNAT-UHFFFAOYSA-N diazoethane Chemical compound CC=[N+]=[N-] WLXALCKAKGDNAT-UHFFFAOYSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- BSQHTIJMZDDKAZ-UHFFFAOYSA-N ethyl 2-(1h-pyrrol-2-yl)acetate Chemical compound CCOC(=O)CC1=CC=CN1 BSQHTIJMZDDKAZ-UHFFFAOYSA-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
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 229960004887 ferric hydroxide Drugs 0.000 description 1
- 239000003527 fibrinolytic agent Substances 0.000 description 1
- 230000004907 flux Effects 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 238000003304 gavage Methods 0.000 description 1
- 235000021552 granulated sugar Nutrition 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- JBSMEKXRTUYEGN-UHFFFAOYSA-N hexyl 6-ethyl-5-(1-propylpyrrole-2-carbonyl)-2,3-dihydro-1H-pyrrolizine-1-carboxylate Chemical compound CCCCCCOC(=O)C1CCN2C1=CC(CC)=C2C(=O)C1=CC=CN1CCC JBSMEKXRTUYEGN-UHFFFAOYSA-N 0.000 description 1
- 150000002431 hydrogen Chemical group 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- IEECXTSVVFWGSE-UHFFFAOYSA-M iron(3+);oxygen(2-);hydroxide Chemical compound [OH-].[O-2].[Fe+3] IEECXTSVVFWGSE-UHFFFAOYSA-M 0.000 description 1
- 229910021506 iron(II) hydroxide Inorganic materials 0.000 description 1
- NCNCGGDMXMBVIA-UHFFFAOYSA-L iron(ii) hydroxide Chemical compound [OH-].[OH-].[Fe+2] NCNCGGDMXMBVIA-UHFFFAOYSA-L 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-O isopropylaminium Chemical compound CC(C)[NH3+] JJWLVOIRVHMVIS-UHFFFAOYSA-O 0.000 description 1
- 239000006193 liquid solution Substances 0.000 description 1
- 239000006194 liquid suspension Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 1
- 229910052808 lithium carbonate Inorganic materials 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- FAWAQIHNFGSGOL-UHFFFAOYSA-N methoxycarbonyl 2-(4-methyl-1h-pyrrol-2-yl)acetate Chemical compound COC(=O)OC(=O)CC1=CC(C)=CN1 FAWAQIHNFGSGOL-UHFFFAOYSA-N 0.000 description 1
- GMKSAIRBTVHGTF-UHFFFAOYSA-N methyl 1-(2-iodoethyl)-2-(2-methoxy-2-oxoethyl)-4-methylpyrrole-3-carboxylate Chemical compound COC(=O)CC1=C(C(=O)OC)C(C)=CN1CCI GMKSAIRBTVHGTF-UHFFFAOYSA-N 0.000 description 1
- RCYRFVQGTJTDQC-UHFFFAOYSA-N methyl 2,3-dihydro-1h-pyrrolizine-1-carboxylate Chemical compound C1=CC=C2C(C(=O)OC)CCN21 RCYRFVQGTJTDQC-UHFFFAOYSA-N 0.000 description 1
- KASVZMDBXFWHOT-UHFFFAOYSA-N methyl 2-(2-methoxy-2-oxoethyl)-4-methyl-1-(2-methylsulfonyloxyethyl)pyrrole-3-carboxylate Chemical compound COC(=O)CC1=C(C(=O)OC)C(C)=CN1CCOS(C)(=O)=O KASVZMDBXFWHOT-UHFFFAOYSA-N 0.000 description 1
- LWIMVOCKGXFWSP-UHFFFAOYSA-N methyl 4-ethyl-1-(2-hydroxyethyl)-2-(2-methoxy-2-oxoethyl)pyrrole-3-carboxylate Chemical compound CCC1=CN(CCO)C(CC(=O)OC)=C1C(=O)OC LWIMVOCKGXFWSP-UHFFFAOYSA-N 0.000 description 1
- PCZMVGYQNXCQAP-UHFFFAOYSA-N methyl 5-(1-methylpyrrole-2-carbonyl)-2,3-dihydro-1H-pyrrolizine-1-carboxylate Chemical compound COC(=O)C1CCN2C1=CC=C2C(=O)C1=CC=CN1C PCZMVGYQNXCQAP-UHFFFAOYSA-N 0.000 description 1
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 229960002216 methylparaben Drugs 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 208000015994 miscarriage Diseases 0.000 description 1
- 230000003387 muscular Effects 0.000 description 1
- ZWRUINPWMLAQRD-UHFFFAOYSA-N n-Nonyl alcohol Natural products CCCCCCCCCO ZWRUINPWMLAQRD-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 210000003739 neck Anatomy 0.000 description 1
- PVSGYRSHEKJTRE-UHFFFAOYSA-N octyl 5-(1-propylpyrrole-2-carbonyl)-2,3-dihydro-1H-pyrrolizine-1-carboxylate Chemical compound CCCCCCCCOC(=O)C1CCN2C1=CC=C2C(=O)C1=CC=CN1CCC PVSGYRSHEKJTRE-UHFFFAOYSA-N 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 229940100692 oral suspension Drugs 0.000 description 1
- 239000007935 oral tablet Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 230000006461 physiological response Effects 0.000 description 1
- 239000000106 platelet aggregation inhibitor Substances 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 208000026440 premature labor Diseases 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical group CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 1
- DHLNRHZOUYOAOD-UHFFFAOYSA-N propan-2-yl 5-(1-butylpyrrole-2-carbonyl)-2,3-dihydro-1H-pyrrolizine-1-carboxylate Chemical compound CCCCN1C=CC=C1C(=O)C1=CC=C2N1CCC2C(=O)OC(C)C DHLNRHZOUYOAOD-UHFFFAOYSA-N 0.000 description 1
- QULKCUSWGSMLGU-UHFFFAOYSA-N propan-2-yl 5-(1-methylpyrrole-2-carbonyl)-2,3-dihydro-1H-pyrrolizine-1-carboxylate Chemical compound CC(C)OC(=O)C1CCN2C1=CC=C2C(=O)C1=CC=CN1C QULKCUSWGSMLGU-UHFFFAOYSA-N 0.000 description 1
- JFRHOHYQEZHVBJ-UHFFFAOYSA-N propan-2-yl 5-(1-propylpyrrole-2-carbonyl)-2,3-dihydro-1H-pyrrolizine-1-carboxylate Chemical compound CCCN1C=CC=C1C(=O)C1=CC=C2N1CCC2C(=O)OC(C)C JFRHOHYQEZHVBJ-UHFFFAOYSA-N 0.000 description 1
- UKBMRTLUEALAHZ-UHFFFAOYSA-N propan-2-yl 5-(1H-pyrrole-2-carbonyl)-2,3-dihydro-1H-pyrrolizine-1-carboxylate Chemical compound CC(C)OC(=O)C1CCN2C1=CC=C2C(=O)C1=CC=CN1 UKBMRTLUEALAHZ-UHFFFAOYSA-N 0.000 description 1
- ROECEILUUKJLTI-UHFFFAOYSA-N propan-2-yl 6-ethyl-5-(1H-pyrrole-2-carbonyl)-2,3-dihydro-1H-pyrrolizine-1-carboxylate Chemical compound CCC=1C=C2C(C(=O)OC(C)C)CCN2C=1C(=O)C1=CC=CN1 ROECEILUUKJLTI-UHFFFAOYSA-N 0.000 description 1
- FPLDXDDBAGZEDE-UHFFFAOYSA-N propan-2-yl 6-propyl-2,3-dihydro-1h-pyrrolizine-1-carboxylate Chemical compound CC(C)OC(=O)C1CCN2C=C(CCC)C=C21 FPLDXDDBAGZEDE-UHFFFAOYSA-N 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- OKWPXDDGBGKEDF-UHFFFAOYSA-N propyl 2,3-dihydro-1h-pyrrolizine-1-carboxylate Chemical compound C1=CC=C2C(C(=O)OCCC)CCN21 OKWPXDDGBGKEDF-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- WRHZVMBBRYBTKZ-UHFFFAOYSA-N pyrrole-2-carboxylic acid Chemical class OC(=O)C1=CC=CN1 WRHZVMBBRYBTKZ-UHFFFAOYSA-N 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- QYXQJKHCQOSQIA-UHFFFAOYSA-M sodium 5-(1-ethylpyrrole-2-carbonyl)-2,3-dihydro-1H-pyrrolizine-1-carboxylate Chemical compound [Na+].CCN1C=CC=C1C(=O)C1=CC=C2N1CCC2C([O-])=O QYXQJKHCQOSQIA-UHFFFAOYSA-M 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- PVFOMCVHYWHZJE-UHFFFAOYSA-N trichloroacetyl chloride Chemical compound ClC(=O)C(Cl)(Cl)Cl PVFOMCVHYWHZJE-UHFFFAOYSA-N 0.000 description 1
- 210000004291 uterus Anatomy 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- UGZADUVQMDAIAO-UHFFFAOYSA-L zinc hydroxide Chemical compound [OH-].[OH-].[Zn+2] UGZADUVQMDAIAO-UHFFFAOYSA-L 0.000 description 1
- 229910021511 zinc hydroxide Inorganic materials 0.000 description 1
- 229940007718 zinc hydroxide Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- 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)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Urology & Nephrology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/783,090 US4097579A (en) | 1977-03-31 | 1977-03-31 | 5-(2-Pyrroyl)-1,2-dihydro-3H-pyrrolo 1,2-a!pyrrole-1-carboxylic acid derivatives and process for the production thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE780605L IE780605L (en) | 1978-09-30 |
| IE46506B1 true IE46506B1 (en) | 1983-06-29 |
Family
ID=25128138
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE605/78A IE46506B1 (en) | 1977-03-31 | 1978-03-29 | 5-(2-pyrroyl)-1,2-dihydro-3h-pyrrolo (1,2-a)pyrrole-1-carboxylic acid derivatives and process for the production thereof |
Country Status (14)
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4140698A (en) * | 1977-07-25 | 1979-02-20 | Syntex (Usa) Inc. | 1,2-Dihydro-3H-pyrrolo[1,2-a]pyrrole-1-nitriles |
| US4232038A (en) * | 1979-08-31 | 1980-11-04 | Syntex (U.S.A.) Inc. | 5-Alkylsulfinylbenzoyl- and 5-alkylsulfonylbenzoyl-1,2-dihydro-3H-pyrrolo[1,]pyrrole-1-carboxylic acids |
| US4344943A (en) * | 1980-06-09 | 1982-08-17 | Syntex (U.S.A.) Inc. | 6-Chloro- or 6-bromo-1,2-dihydro-3H-pyrrolo[1,2-a]-pyrrole-1-carboxylic acids and derivatives thereof |
| US4456759A (en) * | 1980-10-20 | 1984-06-26 | Syntex (U.S.A.) Inc. | 5-Benzoyl-7-halo-1,2-dihydro-3H-pyrrolo-[1,2-a]pyrrole-1,1-dicarboxylic acids and esters thereof |
| US4353829A (en) * | 1980-11-21 | 1982-10-12 | Syntex (U.S.A.) Inc. | Process for 5-aroylation of 1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic esters |
| US4434175A (en) | 1981-08-10 | 1984-02-28 | Merck & Co., Inc. | Nonsteroidal compounds as anti-inflammatory and analgesic agents |
| WO1983001382A1 (en) * | 1981-10-13 | 1983-04-28 | Mroszczak, Edward | Gastrointestinal sparing thioester pro-drugs |
| EP0091181B1 (en) * | 1982-02-25 | 1986-12-17 | Beecham Group Plc | Aroyl pyrrolizine compounds, process for their preparation and pharmaceutical compositions containing them |
| US4457941A (en) * | 1982-03-22 | 1984-07-03 | Syntex (U.S.A.) Inc. | Use of pyrrolo-pyrrole in treating microvascular diseases associated with diabetes |
| US4454151A (en) * | 1982-03-22 | 1984-06-12 | Syntex (U.S.A.) Inc. | Use of pyrrolo pyrroles in treatment of ophthalmic diseases |
| US4612325A (en) * | 1982-06-08 | 1986-09-16 | Syntex (U.S.A) Inc. | 5-Aroyl-6-alkylthio-1,2-dihydro-3H-pyrrolo(1,2-A)pyrrole-1-carboxylic acids and use thereof as analgesics and anti-inflammatories |
| US4511724A (en) * | 1982-06-10 | 1985-04-16 | Merck & Co., Inc. | 5-(Pyrrol-2-oyl)-1,2-dihydro-3H-pyrrolo [1,2-a]pyrrole derivatives as anti-inflammatory and analgesic agents |
| JPS5910589A (ja) * | 1982-06-10 | 1984-01-20 | メルク エンド カムパニー インコーポレーテツド | 抗炎症剤および鎮痛剤として新規な５−（ピロ−ル−２−オイル）−１，２−ジヒドロ−３Ｈ−ピロロ〔１，２−ａ〕ピロ−ル誘導体 |
| US4533671A (en) * | 1982-10-08 | 1985-08-06 | Merck & Co., Inc. | 5-(2,3-Dihydro-1H-pyrrolizin-5-oyl)-2-alkanoic or carboxylic acids and analogs as anti-inflammatory and analgesic agents |
| US4536512A (en) * | 1982-10-08 | 1985-08-20 | Merck & Co., Inc. | 5-(2,3-Dihydro-1H-pyrrolizin-5-oyl)-2,3-dihydro-1H-pyrrolizine-1-alkanoic or carboxylic acids and use thereof as anti-inflammatory and analgesic agents |
| DE3460315D1 (en) * | 1983-02-19 | 1986-08-28 | Beecham Group Plc | Benzofuran and benzothiophene-carboxylic-acid derivatives |
| US4622407A (en) * | 1984-04-26 | 1986-11-11 | Merck & Co., Inc. | Resolution of racemic derivatives of 5-(1-methyl-5-methylthiopyrrol-2-oyl)-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-2-carboxylic acid and analogs |
| US4873340A (en) * | 1986-05-29 | 1989-10-10 | Syntex (U.S.A.) Inc. | Process for preparing 5-aroyl-1,2-dihydro-3H-pyrrolo[1,2-A]pyrrole-1,1-dicarboxylates |
| US4988822A (en) * | 1986-05-29 | 1991-01-29 | Syntex (U.S.A.) Inc. | Intermediates for preparing 5-aroyl-1,2-dihydro-3H-pyrrolo(1,2-A)pyrrole-1,1-dicarboxylates |
| HU198927B (en) * | 1987-01-14 | 1989-12-28 | Richter Gedeon Vegyeszet | Process for producing 1-/substituted aminomethyl/-octa-hydroindolo-(2,3-a)quinolizine derivatives, pharmaceutically applicable acid addition salts thereof, as well as pharmaceutical compositions comprising same |
| US4849526A (en) * | 1987-01-14 | 1989-07-18 | Syntex (U.S.A.) Inc. | Process for preparing (±)-2,3-dihydro-1H-pyrrolo[1,2-A]pyrrole-1,7-dicarboxylates |
| US4874872A (en) * | 1987-01-14 | 1989-10-17 | Syntex (U.S.A.) Inc. | Process for preparing (+)-2,3-dihydro-1H-pyrrolo[1,2-A]pyrrole-1,7-dicarboxylates |
| US4835288A (en) * | 1987-01-14 | 1989-05-30 | Syntex Inc. | Process for preparing (+)-2,3-dihydro-1H-pyrrolo[1,2-a]pyrrole-1,7-dicarboxylates |
| US4874871A (en) * | 1987-03-25 | 1989-10-17 | Syntex (U.S.A.) Inc. | Process for preparing (+)-2,3-Dihydro-1H-pyrrolo[1,2-a]pyrrole-1-carboxylic acid and related compounds |
| US5110493A (en) * | 1987-09-11 | 1992-05-05 | Syntex (U.S.A.) Inc. | Ophthalmic NSAID formulations containing a quaternary ammonium preservative and a nonionic surfactant |
| US5414011A (en) * | 1987-09-11 | 1995-05-09 | Syntex (U.S.A.) Inc. | Preservative system for ophthalmic formulations |
| EP0707465A4 (en) * | 1993-07-08 | 1997-04-16 | Cygnus Therapeutic Systems | MONOLITHIC MATRIX TRANSDERMAL DELIVERY SYSTEM |
| US5621115A (en) * | 1996-02-21 | 1997-04-15 | Ohmeda Pharmaceutical Products Division Inc. | Methods for preparing 5-aroyl-1,2-dihydro-3H-pyrrolo-[1,2-A]pyrrole-1-carboxylic acids |
| US6191285B1 (en) | 1997-07-03 | 2001-02-20 | Abbott Laboratories | Process for the preparation of ketorolac tromethamine |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL293572A (US06815460-20041109-C00103.png) * | 1962-06-07 | |||
| US3846447A (en) * | 1972-08-03 | 1974-11-05 | Mcneilab Inc | Preparation of 5-aroyl-pyrroles and intermediates therefor |
| JPS539789A (en) * | 1976-07-14 | 1978-01-28 | Syntex Inc | Production of 55*22floyl** * 55*22thenoyl** * 55*33 floyl** and 55*33thenoyl** 1*22dihydroo3hhpyroro * 1*22a*pyrolee11carboxylic acid derivative |
-
1977
- 1977-03-31 US US05/783,090 patent/US4097579A/en not_active Expired - Lifetime
-
1978
- 1978-03-23 BE BE186219A patent/BE865247A/xx not_active IP Right Cessation
- 1978-03-27 ES ES468267A patent/ES468267A1/es not_active Expired
- 1978-03-28 DE DE19782813373 patent/DE2813373A1/de active Granted
- 1978-03-28 GB GB12084/78A patent/GB1581411A/en not_active Expired
- 1978-03-29 NZ NZ186797A patent/NZ186797A/xx unknown
- 1978-03-29 CA CA299,870A patent/CA1113938A/en not_active Expired
- 1978-03-29 IE IE605/78A patent/IE46506B1/en unknown
- 1978-03-29 SE SE7803549A patent/SE436648B/sv not_active IP Right Cessation
- 1978-03-30 AU AU34611/78A patent/AU518169B2/en not_active Expired
- 1978-03-30 IT IT67706/78A patent/IT1107833B/it active
- 1978-03-30 FR FR7809294A patent/FR2385719A1/fr active Granted
- 1978-03-30 NL NL7803378A patent/NL7803378A/xx not_active Application Discontinuation
- 1978-03-30 JP JP3616678A patent/JPS53121792A/ja active Granted
-
1979
- 1979-01-02 ES ES476535A patent/ES476535A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB1581411A (en) | 1980-12-10 |
| IT1107833B (it) | 1985-12-02 |
| FR2385719A1 (fr) | 1978-10-27 |
| FR2385719B1 (US06815460-20041109-C00103.png) | 1980-07-18 |
| DE2813373A1 (de) | 1978-10-05 |
| SE436648B (sv) | 1985-01-14 |
| BE865247A (fr) | 1978-09-25 |
| NZ186797A (en) | 1979-12-11 |
| CA1113938A (en) | 1981-12-08 |
| ES476535A1 (es) | 1979-12-01 |
| SE7803549L (sv) | 1978-10-01 |
| JPS647997B2 (US06815460-20041109-C00103.png) | 1989-02-10 |
| ES468267A1 (es) | 1979-10-01 |
| AU518169B2 (en) | 1981-09-17 |
| JPS53121792A (en) | 1978-10-24 |
| US4097579A (en) | 1978-06-27 |
| IE780605L (en) | 1978-09-30 |
| DE2813373C2 (US06815460-20041109-C00103.png) | 1989-11-09 |
| NL7803378A (nl) | 1978-10-03 |
| AU3461178A (en) | 1979-10-04 |
| IT7867706A0 (it) | 1978-03-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| IE46506B1 (en) | 5-(2-pyrroyl)-1,2-dihydro-3h-pyrrolo (1,2-a)pyrrole-1-carboxylic acid derivatives and process for the production thereof | |
| US4089969A (en) | 5-Aroyl-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acid derivatives and process for the production thereof | |
| US4087539A (en) | 5-(2-Furoyl)-, 5-(2-thenoyl)-, 5-(3-furoyl)- and 5-(3-thenoyl)-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acid derivatives and process for the production thereof | |
| US4232038A (en) | 5-Alkylsulfinylbenzoyl- and 5-alkylsulfonylbenzoyl-1,2-dihydro-3H-pyrrolo[1,]pyrrole-1-carboxylic acids | |
| US4344943A (en) | 6-Chloro- or 6-bromo-1,2-dihydro-3H-pyrrolo[1,2-a]-pyrrole-1-carboxylic acids and derivatives thereof | |
| CA1102809A (en) | 5-aroyl-1,2-dihydro-3h-pyrrolo ¬1,2-a|-pyrrole-1- carboxylic acid derivatives and process for the production thereof | |
| US4560699A (en) | 5-(4-Vinylbenzoyl)-1,2-dihydro-3H-pyrrolo-[1,2-a]-pyrrole-1-carboxylic acids and derivatives thereof and use as analgesics and anti-inflammatories | |
| IE45302B1 (en) | 5-(2-furoyl)-,5-(2-thenoyl)-,5(3-furoyl)-and 5-(3-thenoyl)-1,2-dihydro-3h-pyrrolo,2-a)pyrrole-1-carboxylic acid derivatives and process for the production thereof | |
| US4410534A (en) | 3-Substituted-5,6,7,8-tetrahydropyrrolo[1,2-a]-pyridine-and 6,7,8,9-tetrahydro-5H-pyrrolo[1,2-a]-azepine carboxylic acid derivatives useful as blood platelet aggregation inhibitors | |
| US4456759A (en) | 5-Benzoyl-7-halo-1,2-dihydro-3H-pyrrolo-[1,2-a]pyrrole-1,1-dicarboxylic acids and esters thereof | |
| US4000288A (en) | 6,11-dihydrodibenzo-thiepin-11-ones, compositions and uses thereof | |
| US4000308A (en) | 6,11-Dihydrodibenzo-thiepin-11-ones, compositions and uses thereof | |
| US4130654A (en) | Novel 4-(8X-6,11-dihydrodibenzo-[b.e.]-thiepin-11-one-3-yl)-4-oxobutyric acids, methods of preparation, compositions and uses thereof | |
| US4505927A (en) | 5-Benzoyl-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acids and pharmaceutical use thereof | |
| EP0096583B1 (en) | 5-aroyl-1,2-dihydro-3h-pyrrolo 1,2-a pyrrole-1-carboxylic acids and derivatives thereof, processes for their preparation, and intermediates therefor | |
| EP0005055A2 (en) | 6,11-Dihydrodibenzo-thiepin-11-ones and their S-oxides, methods for their preparation and pharmaceutical compositions containing them | |
| DK151336B (da) | Analogifremgangsmaade til fremstilling af en (dl)- eller (l)-5-benzoyl-1,2-dihydro-3h-pyrrol(1,2-a)pyrrol-1-carboxylsyre | |
| DK152653B (da) | Analogifremgangsmaade til fremstilling af (dl)-eller (l)-5-(2-furoyl)-, 5-(2-thenoyl)-, 5-(3-furoyl)- eller 5-(3-thenoyl)-1,2-dihydro-3h-pyrrolooe1,2-aaapyrrol-1-carboxylsyreestere eller salte |