CA1191142A - ¬1R-¬1.alpha.(Z), 2.beta., 3.beta., 5.alpha.||-( )-7-¬5- ¬¬1,1'-BIPHENYL)-4-YL|METHOXY|-3-HYDROXY- 2(1-PIPERIDINYL)CYCLOPENTYL|-4-HEPTENOIC ACID HYDROCHLORIDE - Google Patents

¬1R-¬1.alpha.(Z), 2.beta., 3.beta., 5.alpha.||-( )-7-¬5- ¬¬1,1'-BIPHENYL)-4-YL|METHOXY|-3-HYDROXY- 2(1-PIPERIDINYL)CYCLOPENTYL|-4-HEPTENOIC ACID HYDROCHLORIDE

Info

Publication number: CA1191142A
Authority: CA; Canada
Prior art keywords: beta; alpha; hydroxy; compound; biphenyl
Prior art date: 1982-09-16
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

CA000436773A

Other languages

English (en)

French (fr)

Inventor

Alan Wadsworth

Eric W. Collington

Peter Hallett

Christopher J. Wallis

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.)

Glaxo Group Ltd

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

1985-07-30

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

1985-07-30 Application granted granted Critical

1985-07-30 Publication of CA1191142A publication Critical patent/CA1191142A/en

Status Expired legal-status Critical Current

Links

VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 title claims abstract description 27
ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 title claims description 15
235000010290 biphenyl Nutrition 0.000 title claims description 12
-1 1-PIPERIDINYL Chemical class 0.000 title description 3
BQOWUDKEXDCGQS-UHFFFAOYSA-N [CH]1CCCC1 Chemical compound [CH]1CCCC1 BQOWUDKEXDCGQS-UHFFFAOYSA-N 0.000 title 1
GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 title 1
238000000034 method Methods 0.000 claims description 9
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 8
239000004305 biphenyl Substances 0.000 claims description 7
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 7
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
150000002148 esters Chemical class 0.000 claims description 3
241000555028 Sternidius alpha Species 0.000 claims 6
239000000126 substance Substances 0.000 claims 2
150000001875 compounds Chemical class 0.000 abstract description 18
239000008194 pharmaceutical composition Substances 0.000 abstract description 4
239000002253 acid Substances 0.000 abstract description 3
150000003839 salts Chemical class 0.000 abstract description 3
239000000924 antiasthmatic agent Substances 0.000 abstract description 2
239000003146 anticoagulant agent Substances 0.000 abstract description 2
230000002785 anti-thrombosis Effects 0.000 abstract 1
229940126062 Compound A Drugs 0.000 description 23
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 23
239000000243 solution Substances 0.000 description 23
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
239000000543 intermediate Substances 0.000 description 12
239000000203 mixture Substances 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
230000000694 effects Effects 0.000 description 6
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 5
239000000843 powder Substances 0.000 description 5
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
239000000443 aerosol Substances 0.000 description 4
150000001413 amino acids Chemical class 0.000 description 4
239000002775 capsule Substances 0.000 description 4
238000007907 direct compression Methods 0.000 description 4
239000000284 extract Substances 0.000 description 4
238000002347 injection Methods 0.000 description 4
239000007924 injection Substances 0.000 description 4
239000000463 material Substances 0.000 description 4
OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 4
206010006482 Bronchospasm Diseases 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
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 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
239000004480 active ingredient Substances 0.000 description 3
208000006673 asthma Diseases 0.000 description 3
239000002585 base Substances 0.000 description 3
210000001772 blood platelet Anatomy 0.000 description 3
230000007885 bronchoconstriction Effects 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
239000003814 drug Substances 0.000 description 3
UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
238000001914 filtration Methods 0.000 description 3
239000006260 foam Substances 0.000 description 3
239000008101 lactose Substances 0.000 description 3
235000019359 magnesium stearate Nutrition 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
239000003755 preservative agent Substances 0.000 description 3
230000002335 preservative effect Effects 0.000 description 3
208000010110 spontaneous platelet aggregation Diseases 0.000 description 3
239000000725 suspension Substances 0.000 description 3
239000006188 syrup Substances 0.000 description 3
235000020357 syrup Nutrition 0.000 description 3
WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 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
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
102000008186 Collagen Human genes 0.000 description 2
108010035532 Collagen Proteins 0.000 description 2
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-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
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
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
229920002472 Starch Polymers 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
YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 2
230000037396 body weight Effects 0.000 description 2
DIKBFYAXUHHXCS-UHFFFAOYSA-N bromoform Chemical compound BrC(Br)Br DIKBFYAXUHHXCS-UHFFFAOYSA-N 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
229920001436 collagen Polymers 0.000 description 2
239000003937 drug carrier Substances 0.000 description 2
239000010419 fine particle Substances 0.000 description 2
239000000796 flavoring agent Substances 0.000 description 2
235000019634 flavors Nutrition 0.000 description 2
238000009472 formulation Methods 0.000 description 2
239000007903 gelatin capsule Substances 0.000 description 2
235000011187 glycerol Nutrition 0.000 description 2
QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-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
125000003386 piperidinyl group Chemical group 0.000 description 2
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000002904 solvent Substances 0.000 description 2
239000008107 starch Substances 0.000 description 2
235000019698 starch Nutrition 0.000 description 2
239000005720 sucrose Substances 0.000 description 2
208000019553 vascular disease Diseases 0.000 description 2
238000005550 wet granulation Methods 0.000 description 2
KFXPOIKSDYRVKS-UHFFFAOYSA-N (Z)-4-Heptenoic acid Natural products CCC=CCCC(O)=O KFXPOIKSDYRVKS-UHFFFAOYSA-N 0.000 description 1
BVJYDVKFDDPCAW-UHFFFAOYSA-N 1-aminocyclopentan-1-ol Chemical class NC1(O)CCCC1 BVJYDVKFDDPCAW-UHFFFAOYSA-N 0.000 description 1
UWAOHFMOWBQIJH-UHFFFAOYSA-N 3-cyclopentylpropanal Chemical compound O=CCCC1CCCC1 UWAOHFMOWBQIJH-UHFFFAOYSA-N 0.000 description 1
KFXPOIKSDYRVKS-ONEGZZNKSA-N 4-Heptenoic acid Chemical compound CC\C=C\CCC(O)=O KFXPOIKSDYRVKS-ONEGZZNKSA-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
229920002261 Corn starch Polymers 0.000 description 1
241000065675 Cyclops Species 0.000 description 1
206010012689 Diabetic retinopathy Diseases 0.000 description 1
239000004338 Dichlorodifluoromethane Substances 0.000 description 1
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
244000166102 Eucalyptus leucoxylon Species 0.000 description 1
235000004694 Eucalyptus leucoxylon Nutrition 0.000 description 1
235000019759 Maize starch Nutrition 0.000 description 1
241001465754 Metazoa Species 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
208000010378 Pulmonary Embolism Diseases 0.000 description 1
208000006011 Stroke Diseases 0.000 description 1
208000007536 Thrombosis Diseases 0.000 description 1
238000004220 aggregation Methods 0.000 description 1
230000002776 aggregation 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
239000004411 aluminium Substances 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
229960004676 antithrombotic agent Drugs 0.000 description 1
229940114079 arachidonic acid Drugs 0.000 description 1
235000021342 arachidonic acid Nutrition 0.000 description 1
208000011775 arteriosclerosis disease Diseases 0.000 description 1
239000012298 atmosphere Substances 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
239000012267 brine Substances 0.000 description 1
239000004044 bronchoconstricting agent Substances 0.000 description 1
230000003435 bronchoconstrictive effect Effects 0.000 description 1
239000000872 buffer Substances 0.000 description 1
239000000337 buffer salt Substances 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
229910052681 coesite Inorganic materials 0.000 description 1
238000007906 compression Methods 0.000 description 1
230000006835 compression Effects 0.000 description 1
229910052906 cristobalite Inorganic materials 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
238000000502 dialysis Methods 0.000 description 1
PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 1
235000019404 dichlorodifluoromethane Nutrition 0.000 description 1
229960001760 dimethyl sulfoxide Drugs 0.000 description 1
239000002552 dosage form 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
238000011049 filling Methods 0.000 description 1
230000004927 fusion Effects 0.000 description 1
239000011521 glass Substances 0.000 description 1
239000008187 granular material Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
239000005457 ice water Substances 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
235000019341 magnesium sulphate Nutrition 0.000 description 1
239000002207 metabolite Substances 0.000 description 1
SJFNDMHZXCUXSA-UHFFFAOYSA-M methoxymethyl(triphenyl)phosphanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(COC)C1=CC=CC=C1 SJFNDMHZXCUXSA-UHFFFAOYSA-M 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
239000011812 mixed powder Substances 0.000 description 1
238000002156 mixing Methods 0.000 description 1
208000010125 myocardial infarction Diseases 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
229940094443 oxytocics prostaglandins Drugs 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000000546 pharmaceutical excipient Substances 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
235000015320 potassium carbonate Nutrition 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
230000003389 potentiating effect Effects 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
238000001953 recrystallisation Methods 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
210000002460 smooth muscle Anatomy 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
241000894007 species Species 0.000 description 1
239000007921 spray Substances 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
238000003756 stirring Methods 0.000 description 1
229910052682 stishovite Inorganic materials 0.000 description 1
239000003826 tablet Substances 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
RZWIIPASKMUIAC-VQTJNVASSA-N thromboxane Chemical compound CCCCCCCC[C@H]1OCCC[C@@H]1CCCCCCC RZWIIPASKMUIAC-VQTJNVASSA-N 0.000 description 1
239000002396 thromboxane receptor blocking agent Substances 0.000 description 1
230000001052 transient effect Effects 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
229910052905 tridymite Inorganic materials 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
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
230000002792 vascular Effects 0.000 description 1
239000008215 water for injection Substances 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Hydrogenated Pyridines (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

CA000436773A 1982-09-16 1983-09-15 ¬1R-¬1.alpha.(Z), 2.beta., 3.beta., 5.alpha.||-( )-7-¬5- ¬¬1,1'-BIPHENYL)-4-YL|METHOXY|-3-HYDROXY- 2(1-PIPERIDINYL)CYCLOPENTYL|-4-HEPTENOIC ACID HYDROCHLORIDE Expired CA1191142A (en)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
GB08226378A GB2108116B (en)	1981-09-16	1982-09-16	Aminocyclopentane esters and their preparation and pharmaceutical formulation
GB8226378		1982-09-16
GB8230771		1982-10-28
GB8230771		1982-10-28

Publications (1)

Publication Number	Publication Date
CA1191142A true CA1191142A (en)	1985-07-30

Family

ID=26283848

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000436773A Expired CA1191142A (en)	1982-09-16	1983-09-15	¬1R-¬1.alpha.(Z), 2.beta., 3.beta., 5.alpha.\|\|-( )-7-¬5- ¬¬1,1'-BIPHENYL)-4-YL\|METHOXY\|-3-HYDROXY- 2(1-PIPERIDINYL)CYCLOPENTYL\|-4-HEPTENOIC ACID HYDROCHLORIDE

Country Status (13)

Country	Link
AU (1)	AU576476B2 (de)
CA (1)	CA1191142A (de)
CH (1)	CH655108A5 (de)
DE (1)	DE3333407A1 (de)
FR (1)	FR2533213B1 (de)
HK (1)	HK47689A (de)
IE (1)	IE57366B1 (de)
KE (1)	KE3869A (de)
MY (1)	MY8700837A (de)
NL (1)	NL8303196A (de)
NZ (1)	NZ205609A (de)
SE (1)	SE455094B (de)
SG (1)	SG14389G (de)

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IL62734A (en) *	1980-04-30	1985-10-31	Glaxo Group Ltd	Aminocyclopentane alkenoic acids and esters,their preparation and pharmaceutical formulations
JPS57183772A (en) *	1981-04-29	1982-11-12	Glaxo Group Ltd	Aminocyclopentanol acids and esters, manufacture and medicinal composition
CA1191134A (en) *	1981-04-29	1985-07-30	Eric W. Collington	Aminocyclopentanol acids and esters and their preparation and pharmaceutical formulation
IE53853B1 (en) *	1981-09-16	1989-03-29	Glaxo Group Ltd	Aminocyclopentane esters and their preparation and pharmaceutical formulation
GR77727B (de) *	1981-10-29	1984-09-25	Glaxo Group Ltd
JPS59130282A (ja) *	1982-10-28	1984-07-26	グラクソ・グル−プ・リミテツド	アミノシクロペンタン酸類の製造方法

1983
- 1983-09-09 AU AU19003/83A patent/AU576476B2/en not_active Ceased
- 1983-09-13 FR FR8314526A patent/FR2533213B1/fr not_active Expired
- 1983-09-15 CH CH503383A patent/CH655108A5/de not_active IP Right Cessation
- 1983-09-15 SE SE8304972A patent/SE455094B/sv not_active IP Right Cessation
- 1983-09-15 IE IE216383A patent/IE57366B1/en not_active IP Right Cessation
- 1983-09-15 NZ NZ20560983A patent/NZ205609A/en unknown
- 1983-09-15 DE DE19833333407 patent/DE3333407A1/de not_active Ceased
- 1983-09-15 CA CA000436773A patent/CA1191142A/en not_active Expired
- 1983-09-15 NL NL8303196A patent/NL8303196A/nl not_active Application Discontinuation
1987
- 1987-12-30 MY MY8700837A patent/MY8700837A/xx unknown
1989
- 1989-03-06 KE KE386989A patent/KE3869A/xx unknown
- 1989-03-06 SG SG14389A patent/SG14389G/en unknown
- 1989-06-15 HK HK47689A patent/HK47689A/xx unknown

Also Published As

Publication number	Publication date
KE3869A (en)	1989-06-16
IE832163L (en)	1984-03-16
IE57366B1 (en)	1992-08-12
FR2533213B1 (fr)	1986-10-03
NZ205609A (en)	1986-08-08
HK47689A (en)	1989-06-23
CH655108A5 (de)	1986-03-27
SG14389G (en)	1989-09-22
AU1900383A (en)	1984-03-22
FR2533213A1 (fr)	1984-03-23
SE8304972D0 (sv)	1983-09-15
SE8304972L (sv)	1984-03-17
MY8700837A (en)	1987-12-31
DE3333407A1 (de)	1984-06-20
AU576476B2 (en)	1988-09-01
SE455094B (sv)	1988-06-20
NL8303196A (nl)	1984-04-16

Legal Events

Date	Code	Title	Description
2002-07-31	MKEC	Expiry (correction)
2003-09-15	MKEX	Expiry

Publication	Publication Date	Title
KR100211479B1 (ko)	1999-08-02	3-[2-(디메틸아미노)에틸]-n-메틸-1h-인돌-5-메탄술폰아미드의 비강 투여 제제
US4327092A (en)	1982-04-27	Aminocyclopentane alkenoic acids and esters and pharmaceutical formulations
EP0365119B1 (de)	1994-11-30	Arzneimittel
CH667646A5 (de)	1988-10-31	Aminocyclopentylether, ihre herstellung und pharmazeutische formulierung.
GB2127406A (en)	1984-04-11	Piperidinylcyclopentanolheptenoic acid salt
US3939268A (en)	1976-02-17	2,4-Diamino substituted pyridol(3,2-d)pyrimidine as antithrombotic agents
JPH0352456B2 (de)	1991-08-12
TW200913984A (en)	2009-04-01	Acetamide stereoisomer
CA1313500C (en)	1993-02-09	Pharmaceutical compositions for the treatment of occlusive vascular diseases
EP0111608B1 (de)	1987-03-11	Pseudotropylhalogenbenzoate und ihre Verwendung bei der Behandlung von Migräne
EP0296802A1 (de)	1988-12-28	Aminocyclopentyläther und ihre Herstellung und pharmazeutische Formulierung
IE57366B1 (en)	1992-08-12	Piperidinylcyclopentanol heptenoic acid salt
US4482549A (en)	1984-11-13	Aminocyclopentane esters and pharmaceutical formulation
US4530925A (en)	1985-07-23	Aminocyclopentane esters and pharmaceutical formulations
US4443476A (en)	1984-04-17	Treatment of adult respiratory distress syndrome
JPH0425267B2 (de)	1992-04-30
US4215133A (en)	1980-07-29	2-[N-(2'-Chloro-4'-methyl-thienyl-3')-N-(cyclopropyl-methyl)-amino]-2-imidazoline and salts thereof
ME00246B (de)	2011-05-10	Hfa-suspensionsformulierungen eines anhydrats
WO2012119550A1 (zh)	2012-09-13	含环丙烷结构的c-葡萄糖苷衍生物及其制备方法、药物组合物和用途
EP0351214A1 (de)	1990-01-17	Entzündungshemmende Arylderivate
JPH0314036B2 (de)	1991-02-25
US4977163A (en)	1990-12-11	Aminocyclopentanol acids and esters and their preparation and pharmaceutical formulation
US4478844A (en)	1984-10-23	Bradycardiac or analgesic 2-(N-(thienyl-2-methyl)-N-(2-fluoro-6-methyl-phenyl)-amino)-2-imidazoline and salts thereof
US5039673A (en)	1991-08-13	Aminocyclopentyl ethers and their preparation and pharmaceutical formulation
GB2167404A (en)	1986-05-29	Prostanoid aminocyclopentane alkenoic acids and esters, their preparation and pharmaceutical formulation