CA1068278A - Acide (-)-(3-methyl-4-oxo-5-piperidinothiazolidin-2-ylidene) acetique - Google Patents

Acide (-)-(3-methyl-4-oxo-5-piperidinothiazolidin-2-ylidene) acetique

Info

Publication number: CA1068278A
Authority: CA; Canada
Prior art keywords: ozolinone; methyl; ylidene; oxo; acetic acid
Prior art date: 1977-12-21
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA293,654A

Other languages

English (en)

Inventor

Manfred Herrmann

Wolfgang Steinbrecher

Wolfgang Herrmann

Gerhard Satzinger

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Warner Lambert Co LLC

Original Assignee

Warner Lambert Co LLC

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1977-12-21

Filing date

1977-12-21

Publication date

1979-12-18

1977-12-21 Application filed by Warner Lambert Co LLC filed Critical Warner Lambert Co LLC

1977-12-21 Priority to CA293,654A priority Critical patent/CA1068278A/fr

1979-12-18 Application granted granted Critical

1979-12-18 Publication of CA1068278A publication Critical patent/CA1068278A/fr

Status Expired legal-status Critical Current

Links

NQFBZYYUAFJYNS-UHFFFAOYSA-N 2-(3-methyl-4-oxo-5-piperidin-1-yl-1,3-thiazolidin-2-ylidene)acetic acid Chemical compound S1C(=CC(O)=O)N(C)C(=O)C1N1CCCCC1 NQFBZYYUAFJYNS-UHFFFAOYSA-N 0.000 title claims abstract 3
150000003839 salts Chemical class 0.000 claims abstract description 26
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims abstract description 19
239000000203 mixture Substances 0.000 claims abstract description 7
239000002253 acid Substances 0.000 claims abstract description 6
150000001413 amino acids Chemical class 0.000 claims abstract description 5
238000001640 fractional crystallisation Methods 0.000 claims abstract description 4
150000007524 organic acids Chemical class 0.000 claims abstract description 3
150000007522 mineralic acids Chemical class 0.000 claims abstract 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 39
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
238000000034 method Methods 0.000 claims description 7
239000000243 solution Substances 0.000 claims description 7
238000002360 preparation method Methods 0.000 claims description 6
150000002576 ketones Chemical class 0.000 claims description 4
229960002179 ephedrine Drugs 0.000 claims description 3
239000007864 aqueous solution Substances 0.000 claims description 2
150000008280 chlorinated hydrocarbons Chemical class 0.000 claims description 2
239000004472 Lysine Substances 0.000 claims 1
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 38
NQFBZYYUAFJYNS-FPLPWBNLSA-N (2z)-2-(3-methyl-4-oxo-5-piperidin-1-yl-1,3-thiazolidin-2-ylidene)acetic acid Chemical compound S1\C(=C/C(O)=O)N(C)C(=O)C1N1CCCCC1 NQFBZYYUAFJYNS-FPLPWBNLSA-N 0.000 description 29
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
241000700159 Rattus Species 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
229960000583 acetic acid Drugs 0.000 description 8
230000001882 diuretic effect Effects 0.000 description 8
229950006468 ozolinone Drugs 0.000 description 8
239000002934 diuretic Substances 0.000 description 7
NQFBZYYUAFJYNS-SKVAFPRGSA-N (2Z)-2-[(5R)-3-methyl-4-oxo-5-piperidin-1-yl-1,3-thiazolidin-2-ylidene]acetic acid Chemical compound S1\C(=C/C(O)=O)N(C)C(=O)[C@@H]1N1CCCCC1 NQFBZYYUAFJYNS-SKVAFPRGSA-N 0.000 description 6
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
239000002585 base Substances 0.000 description 5
239000013078 crystal Substances 0.000 description 5
239000003208 petroleum Substances 0.000 description 5
KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
-1 alkyl radical Chemical class 0.000 description 4
150000001875 compounds Chemical class 0.000 description 4
239000002904 solvent Substances 0.000 description 4
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 3
241000282472 Canis lupus familiaris Species 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
230000007059 acute toxicity Effects 0.000 description 3
231100000403 acute toxicity Toxicity 0.000 description 3
238000002474 experimental method Methods 0.000 description 3
239000007787 solid Substances 0.000 description 3
KWGRBVOPPLSCSI-WPRPVWTQSA-N (-)-ephedrine Chemical compound CN[C@@H](C)[C@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WPRPVWTQSA-N 0.000 description 2
241000416162 Astragalus gummifer Species 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
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
229920001615 Tragacanth Polymers 0.000 description 2
239000011149 active material Substances 0.000 description 2
239000000654 additive Substances 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
229940030606 diuretics Drugs 0.000 description 2
230000029142 excretion Effects 0.000 description 2
239000012362 glacial acetic acid Substances 0.000 description 2
229920006158 high molecular weight polymer Polymers 0.000 description 2
238000002347 injection Methods 0.000 description 2
239000007924 injection Substances 0.000 description 2
239000007788 liquid Substances 0.000 description 2
230000007246 mechanism Effects 0.000 description 2
231100000252 nontoxic Toxicity 0.000 description 2
230000003000 nontoxic effect Effects 0.000 description 2
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
239000000725 suspension Substances 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
230000001225 therapeutic effect Effects 0.000 description 2
239000000196 tragacanth Substances 0.000 description 2
235000010487 tragacanth Nutrition 0.000 description 2
229940116362 tragacanth Drugs 0.000 description 2
210000002700 urine Anatomy 0.000 description 2
LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
OQOCQIBPTYHJAK-UHFFFAOYSA-N 2-(1,3-thiazolidin-2-yl)acetic acid Chemical class OC(=O)CC1NCCS1 OQOCQIBPTYHJAK-UHFFFAOYSA-N 0.000 description 1
229920001817 Agar Polymers 0.000 description 1
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 1
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Natural products OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 1
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
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 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
239000001828 Gelatine Substances 0.000 description 1
241000206672 Gelidium Species 0.000 description 1
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 1
229930195725 Mannitol Natural products 0.000 description 1
SMNOERSLNYGGOU-UHFFFAOYSA-N Mefruside Chemical compound C=1C=C(Cl)C(S(N)(=O)=O)=CC=1S(=O)(=O)N(C)CC1(C)CCCO1 SMNOERSLNYGGOU-UHFFFAOYSA-N 0.000 description 1
229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
208000004880 Polyuria Diseases 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000013543 active substance Substances 0.000 description 1
239000002671 adjuvant Substances 0.000 description 1
235000010419 agar Nutrition 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
239000002170 aldosterone antagonist Substances 0.000 description 1
229940083712 aldosterone antagonist Drugs 0.000 description 1
229910001854 alkali hydroxide Inorganic materials 0.000 description 1
229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
150000008041 alkali metal carbonates Chemical class 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
239000011668 ascorbic acid Substances 0.000 description 1
229960005070 ascorbic acid Drugs 0.000 description 1
235000010323 ascorbic acid Nutrition 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000000872 buffer Substances 0.000 description 1
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000001506 calcium phosphate Substances 0.000 description 1
229910000389 calcium phosphate Inorganic materials 0.000 description 1
235000011010 calcium phosphates Nutrition 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
229950005499 carbon tetrachloride Drugs 0.000 description 1
239000012876 carrier material Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000002036 chloroform fraction Substances 0.000 description 1
239000007979 citrate buffer Substances 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
150000004292 cyclic ethers Chemical class 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
230000035619 diuresis Effects 0.000 description 1
238000001035 drying Methods 0.000 description 1
229960001484 edetic acid Drugs 0.000 description 1
230000000694 effects Effects 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 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
239000000706 filtrate Substances 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
235000013355 food flavoring agent Nutrition 0.000 description 1
235000003599 food sweetener Nutrition 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
229960002598 fumaric acid Drugs 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
229940093915 gynecological organic acid Drugs 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
238000002329 infrared spectrum Methods 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
TYQCGQRIZGCHNB-JLAZNSOCSA-N l-ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(O)=C(O)C1=O TYQCGQRIZGCHNB-JLAZNSOCSA-N 0.000 description 1
239000008101 lactose Substances 0.000 description 1
150000002632 lipids Chemical class 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
229960004678 mefruside Drugs 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
235000010981 methylcellulose Nutrition 0.000 description 1
229960002817 metolazone Drugs 0.000 description 1
AQCHWTWZEMGIFD-UHFFFAOYSA-N metolazone Chemical compound CC1NC2=CC(Cl)=C(S(N)(=O)=O)C=C2C(=O)N1C1=CC=CC=C1C AQCHWTWZEMGIFD-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229940068917 polyethylene glycols Drugs 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
230000001376 precipitating effect Effects 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000000746 purification Methods 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000001226 reprecipitation Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
150000003431 steroids Chemical class 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000001117 sulphuric acid Substances 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 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
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
235000019871 vegetable fat Nutrition 0.000 description 1
238000005406 washing Methods 0.000 description 1

Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CA293,654A 1977-12-21 1977-12-21 Acide (-)-(3-methyl-4-oxo-5-piperidinothiazolidin-2-ylidene) acetique Expired CA1068278A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA293,654A CA1068278A (fr)	1977-12-21	1977-12-21	Acide (-)-(3-methyl-4-oxo-5-piperidinothiazolidin-2-ylidene) acetique

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA293,654A CA1068278A (fr)	1977-12-21	1977-12-21	Acide (-)-(3-methyl-4-oxo-5-piperidinothiazolidin-2-ylidene) acetique

Publications (1)

Publication Number	Publication Date
CA1068278A true CA1068278A (fr)	1979-12-18

Family

ID=4110357

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA293,654A Expired CA1068278A (fr)	1977-12-21	1977-12-21	Acide (-)-(3-methyl-4-oxo-5-piperidinothiazolidin-2-ylidene) acetique

Country Status (1)

Country	Link
CA (1)	CA1068278A (fr)

1977
- 1977-12-21 CA CA293,654A patent/CA1068278A/fr not_active Expired

Publication	Publication Date	Title
US4443475A (en)	1984-04-17	Amides of acyl-carnitines, process for preparing same and pharmaceutical compositions containing such amides
DE2444322B2 (de)	1980-08-07	3,63-Substituierte s-Triazolo [4,3-b] pyridazine und Verfahren zu deren Herstellung
IE53493B1 (en)	1988-11-23	New derivatives of pyridazine active on the central nervous system
CA1068278A (fr)	1979-12-18	Acide (-)-(3-methyl-4-oxo-5-piperidinothiazolidin-2-ylidene) acetique
US4683245A (en)	1987-07-28	Laevorotatory antipode of moprolol as an antihypertensive
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PT89637B (pt)	1994-02-28	Processo para a preparacao de derivados de ornitina 5-substituidos e de composicoes farmaceuticas que os contem
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US3580926A (en)	1971-05-25	Carbazole-4-alkanoic acids and tetrahydrocarbazole-4-alkanoic acids
CA1093582A (fr)	1981-01-13	Procede d'obtention de nouvelles propylenediamines
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JPS6360015B2 (fr)	1988-11-22
EP0103500B1 (fr)	1988-01-13	Dérivés de phénéthyl-1alpha-phényl-pipéridine-3-propanenitrile, leur préparation et leur application en thérapeutique
GB1565021A (en)	1980-04-16	Pharmaceutical compositions containing alkylamine deratives
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