CA1045132A - Esters phenyles et naphtyles de prostaglandines - Google Patents

Esters phenyles et naphtyles de prostaglandines

Info

Publication number: CA1045132A
Authority: CA; Canada
Prior art keywords: ester; pge2; produced; optically active; racemic compound
Prior art date: 1973-11-23
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

CA211,341A

Other languages

English (en)

Other versions

CA211341S (en

Inventor

Walter Morozowich

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.)

Pharmacia and Upjohn Co

Original Assignee

Upjohn Co

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.)

1973-11-23

Filing date

1974-10-11

Publication date

1978-12-26

1973-11-23 Priority claimed from US418387A external-priority patent/US3894062A/en

1974-01-08 Priority claimed from US05/431,598 external-priority patent/US3931281A/en

1974-01-08 Priority claimed from US431758A external-priority patent/US3890372A/en

1974-01-08 Priority claimed from US05/431,599 external-priority patent/US3968140A/en

1974-01-08 Priority claimed from US05/431,600 external-priority patent/US3952048A/en

1974-10-11 Application filed by Upjohn Co filed Critical Upjohn Co

1978-12-26 Application granted granted Critical

1978-12-26 Publication of CA1045132A publication Critical patent/CA1045132A/fr

Status Expired legal-status Critical Current

Links

150000003180 prostaglandins Chemical class 0.000 title abstract description 13
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 title abstract description 11
125000001624 naphthyl group Chemical group 0.000 title abstract description 10
229940094443 oxytocics prostaglandins Drugs 0.000 title abstract description 4
238000000034 method Methods 0.000 claims abstract description 127
150000001875 compounds Chemical class 0.000 claims abstract description 102
229960002986 dinoprostone Drugs 0.000 claims abstract description 82
XEYBRNLFEZDVAW-UHFFFAOYSA-N prostaglandin E2 Natural products CCCCCC(O)C=CC1C(O)CC(=O)C1CC=CCCCC(O)=O XEYBRNLFEZDVAW-UHFFFAOYSA-N 0.000 claims abstract description 62
XEYBRNLFEZDVAW-ARSRFYASSA-N dinoprostone Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O XEYBRNLFEZDVAW-ARSRFYASSA-N 0.000 claims abstract description 60
BGKHCLZFGPIKKU-UHFFFAOYSA-N (13E,15S)-15-hydroxy-9-oxo-prosta-10,13-dienoic acid Natural products CCCCCC(O)C=CC1C=CC(=O)C1CCCCCCC(O)=O BGKHCLZFGPIKKU-UHFFFAOYSA-N 0.000 claims abstract description 34
102100036465 Autoimmune regulator Human genes 0.000 claims abstract description 34
101000928549 Homo sapiens Autoimmune regulator Proteins 0.000 claims abstract description 34
BGKHCLZFGPIKKU-LDDQNKHRSA-N prostaglandin A1 Chemical compound CCCCC[C@H](O)\C=C\[C@H]1C=CC(=O)[C@@H]1CCCCCCC(O)=O BGKHCLZFGPIKKU-LDDQNKHRSA-N 0.000 claims abstract description 33
229960000711 alprostadil Drugs 0.000 claims abstract description 32
MYHXHCUNDDAEOZ-UHFFFAOYSA-N Prostaglandin A&2% Natural products CCCCCC(O)C=CC1C=CC(=O)C1CC=CCCCC(O)=O MYHXHCUNDDAEOZ-UHFFFAOYSA-N 0.000 claims abstract description 29
MYHXHCUNDDAEOZ-FOSBLDSVSA-N prostaglandin A2 Chemical compound CCCCC[C@H](O)\C=C\[C@H]1C=CC(=O)[C@@H]1C\C=C/CCCC(O)=O MYHXHCUNDDAEOZ-FOSBLDSVSA-N 0.000 claims abstract description 29
GMVPRGQOIOIIMI-UHFFFAOYSA-N (8R,11R,12R,13E,15S)-11,15-Dihydroxy-9-oxo-13-prostenoic acid Natural products CCCCCC(O)C=CC1C(O)CC(=O)C1CCCCCCC(O)=O GMVPRGQOIOIIMI-UHFFFAOYSA-N 0.000 claims abstract description 17
GMVPRGQOIOIIMI-DWKJAMRDSA-N prostaglandin E1 Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(O)=O GMVPRGQOIOIIMI-DWKJAMRDSA-N 0.000 claims abstract description 16
PXGPLTODNUVGFL-YNNPMVKQSA-N prostaglandin F2alpha Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)C[C@H](O)[C@@H]1C\C=C/CCCC(O)=O PXGPLTODNUVGFL-YNNPMVKQSA-N 0.000 claims abstract 23
101100310593 Candida albicans (strain SC5314 / ATCC MYA-2876) SOD4 gene Proteins 0.000 claims abstract 7
101100190148 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) PGA2 gene Proteins 0.000 claims abstract 7
150000002148 esters Chemical class 0.000 claims description 126
-1 chloroformate ester Chemical class 0.000 claims description 96
MHVJUTLRTHDAOG-UHFFFAOYSA-N p-hydroxyphenylurea Natural products NC(=O)NC1=CC=C(O)C=C1 MHVJUTLRTHDAOG-UHFFFAOYSA-N 0.000 claims description 45
TXFPEBPIARQUIG-UHFFFAOYSA-N 4'-hydroxyacetophenone Chemical compound CC(=O)C1=CC=C(O)C=C1 TXFPEBPIARQUIG-UHFFFAOYSA-N 0.000 claims description 41
QXSAKPUBHTZHKW-UHFFFAOYSA-N 4-hydroxybenzamide Chemical compound NC(=O)C1=CC=C(O)C=C1 QXSAKPUBHTZHKW-UHFFFAOYSA-N 0.000 claims description 37
YOETUEMZNOLGDB-UHFFFAOYSA-N 2-methylpropyl carbonochloridate Chemical group CC(C)COC(Cl)=O YOETUEMZNOLGDB-UHFFFAOYSA-N 0.000 claims description 31
CVPWYDXAVJCNAG-UHFFFAOYSA-N n-(4-hydroxyphenyl)benzamide Chemical compound C1=CC(O)=CC=C1NC(=O)C1=CC=CC=C1 CVPWYDXAVJCNAG-UHFFFAOYSA-N 0.000 claims description 29
NPFYZDNDJHZQKY-UHFFFAOYSA-N 4-Hydroxybenzophenone Chemical compound C1=CC(O)=CC=C1C(=O)C1=CC=CC=C1 NPFYZDNDJHZQKY-UHFFFAOYSA-N 0.000 claims description 28
RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 claims description 28
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 26
USGOUVPJEDUBND-UHFFFAOYSA-N 4-acetamido-n-(4-hydroxyphenyl)benzamide Chemical compound C1=CC(NC(=O)C)=CC=C1C(=O)NC1=CC=C(O)C=C1 USGOUVPJEDUBND-UHFFFAOYSA-N 0.000 claims description 16
NIPKXTKKYSKEON-UHFFFAOYSA-N 4-tritylphenol Chemical compound C1=CC(O)=CC=C1C(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 NIPKXTKKYSKEON-UHFFFAOYSA-N 0.000 claims description 16
VDPCABXJOAHHDE-UHFFFAOYSA-N [(4-hydroxyphenyl)methylideneamino]urea Chemical compound NC(=O)NN=CC1=CC=C(O)C=C1 VDPCABXJOAHHDE-UHFFFAOYSA-N 0.000 claims description 15
XSGQFHNPNWBVPT-VFXMVCAWSA-N 15-methyl-15R-PGE2 Chemical compound CCCCC[C@@](C)(O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O XSGQFHNPNWBVPT-VFXMVCAWSA-N 0.000 claims description 14
RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 claims description 9
150000008064 anhydrides Chemical class 0.000 claims description 9
238000006243 chemical reaction Methods 0.000 claims description 7
UECDWMGGNAYEKF-JTQLQIEISA-N (2s)-n-acetyl-2-amino-3-(4-hydroxyphenyl)propanamide Chemical compound CC(=O)NC(=O)[C@@H](N)CC1=CC=C(O)C=C1 UECDWMGGNAYEKF-JTQLQIEISA-N 0.000 claims description 6
BNMCCUXTLLROIX-AWEZNQCLSA-N n-[(2s)-2-amino-3-(4-hydroxyphenyl)propanoyl]benzamide Chemical compound C([C@H](N)C(=O)NC(=O)C=1C=CC=CC=1)C1=CC=C(O)C=C1 BNMCCUXTLLROIX-AWEZNQCLSA-N 0.000 claims description 6
150000003512 tertiary amines Chemical class 0.000 claims description 5
KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 claims description 2
241001208007 Procas Species 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
230000003287 optical effect Effects 0.000 claims 1
239000002253 acid Substances 0.000 abstract description 14
239000000203 mixture Substances 0.000 abstract description 10
230000000144 pharmacologic effect Effects 0.000 abstract description 5
150000007513 acids Chemical class 0.000 abstract description 4
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 119
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 117
235000013350 formula milk Nutrition 0.000 description 66
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 58
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 51
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 50
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 49
239000000741 silica gel Substances 0.000 description 47
229910002027 silica gel Inorganic materials 0.000 description 47
229960001866 silicon dioxide Drugs 0.000 description 47
238000004809 thin layer chromatography Methods 0.000 description 44
PXGPLTODNUVGFL-BRIYLRKRSA-N (E,Z)-(1R,2R,3R,5S)-7-(3,5-Dihydroxy-2-((3S)-(3-hydroxy-1-octenyl))cyclopentyl)-5-heptenoic acid Chemical compound CCCCC[C@H](O)C=C[C@H]1[C@H](O)C[C@H](O)[C@@H]1CC=CCCCC(O)=O PXGPLTODNUVGFL-BRIYLRKRSA-N 0.000 description 41
229940093499 ethyl acetate Drugs 0.000 description 41
229940086542 triethylamine Drugs 0.000 description 39
235000019439 ethyl acetate Nutrition 0.000 description 38
239000013078 crystal Substances 0.000 description 37
238000010898 silica gel chromatography Methods 0.000 description 33
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 31
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 28
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 21
239000000047 product Substances 0.000 description 20
239000007787 solid Substances 0.000 description 17
CWFVMCXKTWOYKV-UHFFFAOYSA-N 4-benzamido-n-(4-hydroxyphenyl)benzamide Chemical compound C1=CC(O)=CC=C1NC(=O)C(C=C1)=CC=C1NC(=O)C1=CC=CC=C1 CWFVMCXKTWOYKV-UHFFFAOYSA-N 0.000 description 15
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
YXVFYQXJAXKLAK-UHFFFAOYSA-N biphenyl-4-ol Chemical compound C1=CC(O)=CC=C1C1=CC=CC=C1 YXVFYQXJAXKLAK-UHFFFAOYSA-N 0.000 description 14
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 14
239000000243 solution Substances 0.000 description 14
239000002904 solvent Substances 0.000 description 14
ZULJYVVAYGFYKU-UHFFFAOYSA-N acetonitrile;chloroform Chemical compound CC#N.ClC(Cl)Cl ZULJYVVAYGFYKU-UHFFFAOYSA-N 0.000 description 13
UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 description 13
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 13
125000004464 hydroxyphenyl group Chemical group 0.000 description 13
IGWLHPLQBMPWMO-UHFFFAOYSA-N benzene-1,4-diol;benzoic acid Chemical compound OC1=CC=C(O)C=C1.OC(=O)C1=CC=CC=C1 IGWLHPLQBMPWMO-UHFFFAOYSA-N 0.000 description 12
QYBPBEKJXBRSGI-AWEZNQCLSA-N n-[(2s)-1-amino-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]benzamide Chemical compound C([C@@H](C(=O)N)NC(=O)C=1C=CC=CC=1)C1=CC=C(O)C=C1 QYBPBEKJXBRSGI-AWEZNQCLSA-N 0.000 description 12
RJNKBEQRBIJDNM-JTQLQIEISA-N (2s)-2-acetamido-3-(4-hydroxyphenyl)propanamide Chemical compound CC(=O)N[C@H](C(N)=O)CC1=CC=C(O)C=C1 RJNKBEQRBIJDNM-JTQLQIEISA-N 0.000 description 11
XFZCWYQDCUVTFY-UHFFFAOYSA-N (4-hydroxynaphthalen-1-yl)urea Chemical compound C1=CC=C2C(NC(=O)N)=CC=C(O)C2=C1 XFZCWYQDCUVTFY-UHFFFAOYSA-N 0.000 description 11
150000004702 methyl esters Chemical class 0.000 description 11
PKXMBSGDVCDSSB-UHFFFAOYSA-N n-(3-acetamido-4-hydroxyphenyl)acetamide Chemical compound CC(=O)NC1=CC=C(O)C(NC(C)=O)=C1 PKXMBSGDVCDSSB-UHFFFAOYSA-N 0.000 description 11
FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 10
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 10
LLODYIVTBQCBBR-UHFFFAOYSA-N n-(4-hydroxynaphthalen-1-yl)benzamide Chemical compound C12=CC=CC=C2C(O)=CC=C1NC(=O)C1=CC=CC=C1 LLODYIVTBQCBBR-UHFFFAOYSA-N 0.000 description 10
239000003921 oil Substances 0.000 description 10
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 10
BNIXCWKOADUVSB-UHFFFAOYSA-N 1-(4-hydroxyphenyl)-3-phenylurea Chemical compound C1=CC(O)=CC=C1NC(=O)NC1=CC=CC=C1 BNIXCWKOADUVSB-UHFFFAOYSA-N 0.000 description 8
SDWUMTZYWKRIRA-UHFFFAOYSA-N 4-hydroxy-n-(4-tritylphenyl)benzamide Chemical compound C1=CC(O)=CC=C1C(=O)NC1=CC=C(C(C=2C=CC=CC=2)(C=2C=CC=CC=2)C=2C=CC=CC=2)C=C1 SDWUMTZYWKRIRA-UHFFFAOYSA-N 0.000 description 8
238000007792 addition Methods 0.000 description 8
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 8
239000012074 organic phase Substances 0.000 description 8
238000002360 preparation method Methods 0.000 description 7
229940022663 acetate Drugs 0.000 description 6
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
NBEMQPLNBYYUAZ-UHFFFAOYSA-N ethyl acetate;propan-2-one Chemical compound CC(C)=O.CCOC(C)=O NBEMQPLNBYYUAZ-UHFFFAOYSA-N 0.000 description 6
LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 6
229940090248 4-hydroxybenzoic acid Drugs 0.000 description 5
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 5
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 5
NRDQFWXVTPZZAZ-UHFFFAOYSA-N butyl carbonochloridate Chemical compound CCCCOC(Cl)=O NRDQFWXVTPZZAZ-UHFFFAOYSA-N 0.000 description 5
238000004587 chromatography analysis Methods 0.000 description 5
MHYCRLGKOZWVEF-UHFFFAOYSA-N ethyl acetate;hydrate Chemical compound O.CCOC(C)=O MHYCRLGKOZWVEF-UHFFFAOYSA-N 0.000 description 5
KBJFWKRDRSFIBS-UHFFFAOYSA-N n-(4-hydroxynaphthalen-1-yl)acetamide Chemical compound C1=CC=C2C(NC(=O)C)=CC=C(O)C2=C1 KBJFWKRDRSFIBS-UHFFFAOYSA-N 0.000 description 5
229960003010 sodium sulfate Drugs 0.000 description 5
229910052938 sodium sulfate Inorganic materials 0.000 description 5
235000011152 sodium sulphate Nutrition 0.000 description 5
230000009897 systematic effect Effects 0.000 description 5
241001465754 Metazoa Species 0.000 description 4
125000000217 alkyl group Chemical group 0.000 description 4
238000002425 crystallisation Methods 0.000 description 4
230000008025 crystallization Effects 0.000 description 4
150000002989 phenols Chemical class 0.000 description 4
QCXJEYYXVJIFCE-UHFFFAOYSA-N 4-acetamidobenzoic acid Chemical compound CC(=O)NC1=CC=C(C(O)=O)C=C1 QCXJEYYXVJIFCE-UHFFFAOYSA-N 0.000 description 3
PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
KSZVHVUMUSIKTC-UHFFFAOYSA-N acetic acid;propan-2-one Chemical compound CC(C)=O.CC(O)=O KSZVHVUMUSIKTC-UHFFFAOYSA-N 0.000 description 3
XLUXHEZIGIDTCC-UHFFFAOYSA-N acetonitrile;ethyl acetate Chemical compound CC#N.CCOC(C)=O XLUXHEZIGIDTCC-UHFFFAOYSA-N 0.000 description 3
239000003153 chemical reaction reagent Substances 0.000 description 3
238000000354 decomposition reaction Methods 0.000 description 3
150000004780 naphthols Chemical class 0.000 description 3
ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 3
BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 2
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
101100025412 Arabidopsis thaliana XI-A gene Proteins 0.000 description 2
101100515520 Arabidopsis thaliana XI-J gene Proteins 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
241000124008 Mammalia Species 0.000 description 2
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
206010000210 abortion Diseases 0.000 description 2
231100000176 abortion Toxicity 0.000 description 2
MOQOOKGPCBQMCY-UHFFFAOYSA-N acetic acid;hexane Chemical compound CC(O)=O.CCCCCC MOQOOKGPCBQMCY-UHFFFAOYSA-N 0.000 description 2
125000005907 alkyl ester group Chemical group 0.000 description 2
125000005037 alkyl phenyl group Chemical group 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
230000004071 biological effect Effects 0.000 description 2
230000036772 blood pressure Effects 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
239000012230 colorless oil Substances 0.000 description 2
239000012043 crude product Substances 0.000 description 2
INCWELKXTZCRSA-UHFFFAOYSA-N ethyl acetate;methanol;hydrate Chemical compound O.OC.CCOC(C)=O INCWELKXTZCRSA-UHFFFAOYSA-N 0.000 description 2
WHQLQYRFIHPMNA-UHFFFAOYSA-N ethyl acetate;oxolane Chemical compound C1CCOC1.CCOC(C)=O WHQLQYRFIHPMNA-UHFFFAOYSA-N 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
230000002496 gastric effect Effects 0.000 description 2
239000000499 gel Substances 0.000 description 2
238000005227 gel permeation chromatography Methods 0.000 description 2
MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 2
229940064471 heptanoic acid Drugs 0.000 description 2
125000004356 hydroxy functional group Chemical group O* 0.000 description 2
230000006698 induction Effects 0.000 description 2
150000002500 ions Chemical class 0.000 description 2
239000007788 liquid Substances 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
230000028327 secretion Effects 0.000 description 2
150000007659 semicarbazones Chemical class 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
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NHADDZMCASKINP-HTRCEHHLSA-N decarboxydihydrocitrinin Natural products C1=C(O)C(C)=C2[C@H](C)[C@@H](C)OCC2=C1O NHADDZMCASKINP-HTRCEHHLSA-N 0.000 description 1
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NIQQIJXGUZVEBB-UHFFFAOYSA-N methanol;propan-2-one Chemical compound OC.CC(C)=O NIQQIJXGUZVEBB-UHFFFAOYSA-N 0.000 description 1
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WYMSBXTXOHUIGT-UHFFFAOYSA-N paraoxon Chemical compound CCOP(=O)(OCC)OC1=CC=C([N+]([O-])=O)C=C1 WYMSBXTXOHUIGT-UHFFFAOYSA-N 0.000 description 1
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NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
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OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C405/00—Compounds containing a five-membered ring having two side-chains in ortho position to each other, and having oxygen atoms directly attached to the ring in ortho position to one of the side-chains, one side-chain containing, not directly attached to the ring, a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, and the other side-chain having oxygen atoms attached in gamma-position to the ring, e.g. prostaglandins ; Analogues or derivatives thereof
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Life Sciences & Earth Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Engineering & Computer Science (AREA)
Pharmacology & Pharmacy (AREA)
Bioinformatics & Cheminformatics (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CA211,341A 1973-11-23 1974-10-11 Esters phenyles et naphtyles de prostaglandines Expired CA1045132A (fr)

Applications Claiming Priority (5)

Application Number	Priority Date	Filing Date	Title
US418387A US3894062A (en)	1973-11-23	1973-11-23	Substituted phenyl and naphthyl esters of PGE{HD 2
US05/431,598 US3931281A (en)	1974-01-08	1974-01-08	Substituted anilide ester of PGA2
US431758A US3890372A (en)	1974-01-08	1974-01-08	Amino substituted phenyl and naphthyl esters of PGF{HD 2{301 {B - type compounds
US05/431,599 US3968140A (en)	1974-01-08	1974-01-08	Substituted anilide esters of PGE1
US05/431,600 US3952048A (en)	1974-01-08	1974-01-08	Substituted anilide esters of PGA

Publications (1)

Publication Number	Publication Date
CA1045132A true CA1045132A (fr)	1978-12-26

Family

ID=27541538

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA211,341A Expired CA1045132A (fr)	1973-11-23	1974-10-11	Esters phenyles et naphtyles de prostaglandines

Country Status (8)

Country	Link
JP (1)	JPS5757472B2 (fr)
BE (1)	BE822514A (fr)
CA (1)	CA1045132A (fr)
DE (1)	DE2453271A1 (fr)
FR (1)	FR2252094B1 (fr)
GB (1)	GB1436300A (fr)
NL (1)	NL7415248A (fr)
SE (1)	SE422056B (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3998869A (en) *	1974-11-14	1976-12-21	The Upjohn Company	Substituted anilide esters of 16-substituted PGE2
EP4055007A4 (fr) *	2019-11-07	2024-02-14	Lifex Biolabs, Inc.	Analogues de la prostaglandine et leurs utilisations

1974
- 1974-10-11 CA CA211,341A patent/CA1045132A/fr not_active Expired
- 1974-11-09 DE DE19742453271 patent/DE2453271A1/de not_active Withdrawn
- 1974-11-21 GB GB5043974A patent/GB1436300A/en not_active Expired
- 1974-11-21 JP JP49133251A patent/JPS5757472B2/ja not_active Expired
- 1974-11-22 SE SE7414711A patent/SE422056B/xx unknown
- 1974-11-22 BE BE150781A patent/BE822514A/fr not_active IP Right Cessation
- 1974-11-22 FR FR7438411A patent/FR2252094B1/fr not_active Expired
- 1974-11-22 NL NL7415248A patent/NL7415248A/xx not_active Application Discontinuation

Also Published As

Publication number	Publication date
FR2252094B1 (fr)	1978-08-18
GB1436300A (en)	1976-05-19
SE7414711L (fr)	1975-05-26
JPS5757472B2 (fr)	1982-12-04
FR2252094A1 (fr)	1975-06-20
NL7415248A (nl)	1975-05-27
DE2453271A1 (de)	1975-05-28
SE422056B (sv)	1982-02-15
BE822514A (fr)	1975-05-22
JPS5083351A (fr)	1975-07-05

Publication	Publication Date	Title
JP2004529973A (ja)	2004-09-30	１７−フェニル−１８，１９，２０−トリノル−ＰＧＦ２αおよびその誘導体の新製法
IL43589A (en)	1980-01-31	16-phenoxy-15-hydroxy derivatives of 17,18,19,20-tetranorprostaglandins and their preparation
US3894062A (en)	1975-07-08	Substituted phenyl and naphthyl esters of PGE{HD 2
CA1045132A (fr)	1978-12-26	Esters phenyles et naphtyles de prostaglandines
US3931285A (en)	1976-01-06	Substituted tolyl esters of PGE1
US4783480A (en)	1988-11-08	6-keto-prostaglandin E1 derivatives
US4100192A (en)	1978-07-11	Inter-phenylene-PG amides
US3998869A (en)	1976-12-21	Substituted anilide esters of 16-substituted PGE2
US3988355A (en)	1976-10-26	Substituted phenyl and naphthyl esters of PGE1
US3890372A (en)	1975-06-17	Amino substituted phenyl and naphthyl esters of PGF{HD 2{301 {B - type compounds
EP0386901A1 (fr)	1990-09-12	Dérivés 5-hétéro-6-oxo-PGE
US4099015A (en)	1978-07-04	2,2-Difluoro-13,14-didehydro-11-deoxy-17-phenyl-18,19,20-trinor-PGE2 compounds
US3994956A (en)	1976-11-30	Substituted anilide esters of 16-phenoxy and 17-phenyl PGE2 type compounds
US3987067A (en)	1976-10-19	Substituted aromatic esters of PGF2.sub.α
CA1059506A (fr)	1979-07-31	Preparation d'esters phenacyliques d'acides prostanoiques
EP0471856B1 (fr)	1995-03-22	Derive de 15-desoxyprostaglandine
KR0133050B1 (ko)	1998-04-17	프로스타글란딘 중간체의 제조방법
US3959319A (en)	1976-05-25	Phenyl and naphthyl esters of PGF2 α type prostaglandins
US4012427A (en)	1977-03-15	Substituted phenyl esters of PGE1 -type prostaglandins
US3948970A (en)	1976-04-06	Substituted tolyl esters of PGA1
US3931281A (en)	1976-01-06	Substituted anilide ester of PGA2
US3968140A (en)	1976-07-06	Substituted anilide esters of PGE1
US4011249A (en)	1977-03-08	Substituted keto and alkoxy carbonyl esters of 16-substituted PGE2 type compounds
US4013707A (en)	1977-03-22	Substituted phenyl esters of PGA1
US3962289A (en)	1976-06-08	Esters of PGA2 and p-tritylphenol