BE897763A - Sel de l'acide piperidinyl-cyclopentanol heptenoique - Google Patents

Sel de l'acide piperidinyl-cyclopentanol heptenoique Download PDF

Info

Publication number: BE897763A
Authority: BE; Belgium
Prior art keywords: sep; compound; solution; compound according; acid
Prior art date: 1982-09-16

Application number

BE0/211540A

Other languages

English (en)

French (fr)

Original Assignee

Glaxo Group Ltd

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.)

1982-09-16

Filing date

1983-09-15

Publication date

1984-03-15

1982-09-16 Priority claimed from GB08226378A external-priority patent/GB2108116B/en

1983-09-15 Application filed by Glaxo Group Ltd filed Critical Glaxo Group Ltd

1984-03-15 Publication of BE897763A publication Critical patent/BE897763A/fr

Links

ZPWADKSVVTUPFP-UHFFFAOYSA-N C(C=CCCCC)(=O)O.N1(CCCCC1)C1(CCCC1)O Chemical compound C(C=CCCCC)(=O)O.N1(CCCCC1)C1(CCCC1)O ZPWADKSVVTUPFP-UHFFFAOYSA-N 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 32
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 20
239000002253 acid Substances 0.000 claims abstract description 10
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 8
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims abstract description 7
239000000924 antiasthmatic agent Substances 0.000 claims abstract description 4
235000010290 biphenyl Nutrition 0.000 claims abstract description 4
239000003146 anticoagulant agent Substances 0.000 claims abstract description 3
230000002785 anti-thrombosis Effects 0.000 claims abstract 2
239000000243 solution Substances 0.000 claims description 24
239000000203 mixture Substances 0.000 claims description 21
239000000443 aerosol Substances 0.000 claims description 6
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 6
229910000041 hydrogen chloride Inorganic materials 0.000 claims description 6
238000002347 injection Methods 0.000 claims description 6
239000007924 injection Substances 0.000 claims description 6
239000000843 powder Substances 0.000 claims description 6
239000006188 syrup Substances 0.000 claims description 6
235000020357 syrup Nutrition 0.000 claims description 6
239000004305 biphenyl Substances 0.000 claims description 5
239000002775 capsule Substances 0.000 claims description 5
239000000546 pharmaceutical excipient Substances 0.000 claims description 4
239000007921 spray Substances 0.000 claims description 3
239000003937 drug carrier Substances 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims 1
-1 (1-piperidinyl) cyclopentyl Chemical group 0.000 abstract description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
229940126062 Compound A Drugs 0.000 description 18
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 18
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
239000000543 intermediate Substances 0.000 description 16
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
239000003826 tablet Substances 0.000 description 10
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 7
239000000284 extract Substances 0.000 description 5
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 4
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
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 4
229920002472 Starch Polymers 0.000 description 4
239000004480 active ingredient Substances 0.000 description 4
150000001413 amino acids Chemical class 0.000 description 4
238000007907 direct compression Methods 0.000 description 4
239000008101 lactose Substances 0.000 description 4
235000019359 magnesium stearate Nutrition 0.000 description 4
239000000463 material Substances 0.000 description 4
238000002360 preparation method Methods 0.000 description 4
239000008107 starch Substances 0.000 description 4
235000019698 starch Nutrition 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000002585 base Substances 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
238000007906 compression Methods 0.000 description 3
230000006835 compression Effects 0.000 description 3
239000003814 drug Substances 0.000 description 3
230000000694 effects Effects 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
238000011049 filling Methods 0.000 description 3
239000006260 foam Substances 0.000 description 3
230000008018 melting Effects 0.000 description 3
238000002844 melting Methods 0.000 description 3
238000000034 method Methods 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
239000000725 suspension Substances 0.000 description 3
WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 2
LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 2
QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 2
206010006482 Bronchospasm Diseases 0.000 description 2
102000008186 Collagen Human genes 0.000 description 2
108010035532 Collagen Proteins 0.000 description 2
239000004338 Dichlorodifluoromethane Substances 0.000 description 2
239000007832 Na2SO4 Substances 0.000 description 2
239000005642 Oleic acid Substances 0.000 description 2
ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-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
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
229930006000 Sucrose Natural products 0.000 description 2
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 2
239000008346 aqueous phase Substances 0.000 description 2
208000006673 asthma Diseases 0.000 description 2
DIKBFYAXUHHXCS-UHFFFAOYSA-N bromoform Chemical compound BrC(Br)Br DIKBFYAXUHHXCS-UHFFFAOYSA-N 0.000 description 2
230000007885 bronchoconstriction Effects 0.000 description 2
239000000872 buffer Substances 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
229920001436 collagen Polymers 0.000 description 2
PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 2
235000019404 dichlorodifluoromethane Nutrition 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
238000001914 filtration Methods 0.000 description 2
239000010419 fine particle Substances 0.000 description 2
239000012530 fluid Substances 0.000 description 2
239000007903 gelatin capsule Substances 0.000 description 2
235000011187 glycerol Nutrition 0.000 description 2
239000008187 granular material Substances 0.000 description 2
QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 2
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
239000012071 phase Substances 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
239000003755 preservative agent Substances 0.000 description 2
230000002335 preservative effect Effects 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000002904 solvent Substances 0.000 description 2
239000005720 sucrose Substances 0.000 description 2
RZWIIPASKMUIAC-VQTJNVASSA-N thromboxane Chemical compound CCCCCCCC[C@H]1OCCC[C@@H]1CCCCCCC RZWIIPASKMUIAC-VQTJNVASSA-N 0.000 description 2
BVJYDVKFDDPCAW-UHFFFAOYSA-N 1-aminocyclopentan-1-ol Chemical compound NC1(O)CCCC1 BVJYDVKFDDPCAW-UHFFFAOYSA-N 0.000 description 1
206010002383 Angina Pectoris Diseases 0.000 description 1
206010003210 Arteriosclerosis Diseases 0.000 description 1
201000001320 Atherosclerosis Diseases 0.000 description 1
NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
208000024172 Cardiovascular disease Diseases 0.000 description 1
241000700198 Cavia Species 0.000 description 1
241000700199 Cavia porcellus Species 0.000 description 1
206010012689 Diabetic retinopathy Diseases 0.000 description 1
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
235000004694 Eucalyptus leucoxylon Nutrition 0.000 description 1
244000166102 Eucalyptus leucoxylon Species 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
229920000168 Microcrystalline cellulose Polymers 0.000 description 1
229920000881 Modified starch Polymers 0.000 description 1
208000018262 Peripheral vascular disease Diseases 0.000 description 1
206010050902 Postoperative thrombosis Diseases 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
208000010378 Pulmonary Embolism Diseases 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
208000007536 Thrombosis Diseases 0.000 description 1
208000032109 Transient ischaemic attack Diseases 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000004523 agglutinating effect Effects 0.000 description 1
230000004520 agglutination Effects 0.000 description 1
239000003513 alkali Substances 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
229910052782 aluminium 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
230000003042 antagnostic effect Effects 0.000 description 1
229960004676 antithrombotic agent Drugs 0.000 description 1
YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical class CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 1
208000011775 arteriosclerosis disease Diseases 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
125000006267 biphenyl group Chemical group 0.000 description 1
SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 1
230000037396 body weight Effects 0.000 description 1
239000012267 brine Substances 0.000 description 1
239000004044 bronchoconstricting agent Substances 0.000 description 1
230000003435 bronchoconstrictive effect Effects 0.000 description 1
239000000337 buffer salt Substances 0.000 description 1
208000026106 cerebrovascular disease Diseases 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000003086 colorant Substances 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
238000000502 dialysis Methods 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
231100000673 dose–response relationship Toxicity 0.000 description 1
229940079593 drug Drugs 0.000 description 1
238000001035 drying Methods 0.000 description 1
238000005538 encapsulation Methods 0.000 description 1
125000004494 ethyl ester group Chemical group 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
235000013305 food Nutrition 0.000 description 1
235000013355 food flavoring agent Nutrition 0.000 description 1
239000011521 glass Substances 0.000 description 1
238000005469 granulation Methods 0.000 description 1
230000003179 granulation Effects 0.000 description 1
CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 1
239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 1
239000005457 ice water Substances 0.000 description 1
238000010348 incorporation Methods 0.000 description 1
238000001802 infusion Methods 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
JGPXULUSWLHRSO-UHFFFAOYSA-N methoxymethyl(diphenyl)phosphanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1[PH+](COC)C1=CC=CC=C1 JGPXULUSWLHRSO-UHFFFAOYSA-N 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
235000019813 microcrystalline cellulose Nutrition 0.000 description 1
239000008108 microcrystalline cellulose Substances 0.000 description 1
229940016286 microcrystalline cellulose Drugs 0.000 description 1
208000010125 myocardial infarction Diseases 0.000 description 1
239000006199 nebulizer Substances 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
229940094443 oxytocics prostaglandins Drugs 0.000 description 1
238000004806 packaging method and process Methods 0.000 description 1
229940124531 pharmaceutical excipient Drugs 0.000 description 1
DOIRQSBPFJWKBE-UHFFFAOYSA-N phthalic acid di-n-butyl ester Natural products CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 1
210000002381 plasma Anatomy 0.000 description 1
210000004623 platelet-rich plasma Anatomy 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
235000015320 potassium carbonate Nutrition 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
230000002265 prevention Effects 0.000 description 1
150000003180 prostaglandins Chemical class 0.000 description 1
239000008213 purified water Substances 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
238000012797 qualification Methods 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
210000002460 smooth muscle Anatomy 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
239000012453 solvate Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
201000010875 transient cerebral ischemia Diseases 0.000 description 1
CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
229940029284 trichlorofluoromethane Drugs 0.000 description 1
JBWKIWSBJXDJDT-UHFFFAOYSA-N triphenylmethyl chloride Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 JBWKIWSBJXDJDT-UHFFFAOYSA-N 0.000 description 1
238000001665 trituration Methods 0.000 description 1
230000002792 vascular Effects 0.000 description 1
208000019553 vascular disease Diseases 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
238000005550 wet granulation Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/14—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D295/155—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors

Landscapes

Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Bioinformatics & Cheminformatics (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Engineering & Computer Science (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Hematology (AREA)
Diabetes (AREA)
Pulmonology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

BE0/211540A 1982-09-16 1983-09-15 Sel de l'acide piperidinyl-cyclopentanol heptenoique BE897763A (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB08226378A GB2108116B (en)	1981-09-16	1982-09-16	Aminocyclopentane esters and their preparation and pharmaceutical formulation

Publications (1)

Publication Number	Publication Date
BE897763A true BE897763A (fr)	1984-03-15

Family

ID=10532940

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
BE0/211540A BE897763A (fr)	1982-09-16	1983-09-15	Sel de l'acide piperidinyl-cyclopentanol heptenoique

Country Status (2)

Country	Link
JP (1)	JPS5973576A (ja)
BE (1)	BE897763A (ja)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NO885689L (no) *	1987-12-22	1989-06-23	Glaxo Group Ltd	Fremgangsmaate for fremstilling av vandige preparater inneholdende et piperidinylcyklopentyl-heptensyrederivat.
TWI592159B (zh) *	2007-11-16	2017-07-21	威佛（國際）股份有限公司	藥學組成物

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
BE877595A (fr) *	1978-07-11	1980-01-10	Glaxo Group Ltd	Nouveaux prostenoides et procede pour leur preparation
JPS57183772A (en) *	1981-04-29	1982-11-12	Glaxo Group Ltd	Aminocyclopentanol acids and esters, manufacture and medicinal composition

1983
- 1983-09-14 JP JP58168497A patent/JPS5973576A/ja active Granted
- 1983-09-15 BE BE0/211540A patent/BE897763A/fr not_active IP Right Cessation

Also Published As

Publication number	Publication date
JPS5973576A (ja)	1984-04-25
JPH0425267B2 (ja)	1992-04-30

Legal Events

Date

Code

Title

Description

1997-03-31

RE

Patent lapsed

Owner name: GLAXO GROUP LTD

Effective date: 19960930

Publication	Publication Date	Title
US3885046A (en)	1975-05-20	Meta chloro or fluoro substituted alpha-T-butylaminopropionphenones in the treatment of depression
US3819706A (en)	1974-06-25	Meta chloro substituted-alpha-butylamino-propiophenones
JPS6121550B2 (ja)	1986-05-27
FR2530625A1 (fr)	1984-01-27	Derives d'indole, procedes pour leur preparation et compositions pharmaceutiques les contenant
NL8802059A (nl)	1989-03-16	Esters en amiden van cyclische carbonzuren en cyclische alcoholen en aminen.
FR2503702A1 (fr)	1982-10-15	Nouveaux cycloalcane-amides a substituants adjacents, doues de proprietes analgesiques et compositions pharmaceutiques les contenant
PL154186B1 (en)	1991-07-31	Method for manufacturing arylic derivatives of the hydroxamic acid
KR100513302B1 (ko)	2005-11-11	3-아미노-1,2-벤조이소옥사졸 유도체, 이의 제조방법및 용도
FR2564464A1 (fr)	1985-11-22	Ethers aminocyclopentyliques, leur procede de fabrication et composition pharmaceutique en resultant
MC1156A1 (fr)	1978-04-17	Composes cycliques
BE897763A (fr)	1984-03-15	Sel de l'acide piperidinyl-cyclopentanol heptenoique
EP1682124B1 (fr)	2007-12-19	Compositions pharmaceutiques a base de sel d'idazoxan ou d´un de ses polymorphes
US3953601A (en)	1976-04-27	Dibenzothiophene derivatives as serum lipid lowering agents
GB2127406A (en)	1984-04-11	Piperidinylcyclopentanolheptenoic acid salt
FR2533213A1 (fr)	1984-03-23	Sel d'acide piperidinylcyclopentanolheptenoique, son procede de preparation et son utilisation therapeutique
JPH05331129A (ja)	1993-12-14	カフェー酸誘導体及びそれを含む医薬組成物
JPH0240063B2 (ja)	1990-09-10
FR2551440A1 (fr)	1985-03-08	Aminocyclopentanes, leur procede de preparation et compositions pharmaceutiques les contenant
MC1287A1 (fr)	1980-07-22	Derives de cyclohexadiene
JPS5883694A (ja)	1983-05-19	８−ベンゾイルアミノアルキルピロリチジン誘導体
JPH0127073B2 (ja)	1989-05-26
JPS6056974A (ja)	1985-04-02	環式ジチオジアセトアミドおよびその製造方法並びに薬剤
FR2624120A1 (fr)	1989-06-09	Nouveaux sels organogermaniques utiles comme medicaments notamment comme activateurs des osteoblastes
CN103304502B (zh)	2015-03-04	一类抗糖尿病化合物、其制备方法和用途
BE845963A (fr)	1977-03-08	Amidrazones vinylogues, procede pour leur preparation et medicament contenant ceux-ci