CA1249999A - Composes d'enamide acyles, preparations pharmaceutiques les contenant, applications de ces preparations et procede de production - Google Patents

Composes d'enamide acyles, preparations pharmaceutiques les contenant, applications de ces preparations et procede de production

Info

Publication number: CA1249999A
Authority: CA; Canada
Prior art keywords: compounds; acylated; acylated enamide; formula; pharmaceutical compositions
Prior art date: 1984-06-26
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

CA000457455A

Other languages

English (en)

Inventor

Heinz Viehe

Francoise Hervens

Marcel Roberfroid

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.)

Biotec AB

Original Assignee

Biotec AB

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.)

1984-06-26

Filing date

1984-06-26

Publication date

1989-02-14

1984-06-26 Application filed by Biotec AB filed Critical Biotec AB

1984-06-26 Priority to CA000457455A priority Critical patent/CA1249999A/fr

1989-02-14 Application granted granted Critical

1989-02-14 Publication of CA1249999A publication Critical patent/CA1249999A/fr

Status Expired legal-status Critical Current

Links

239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 33
125000005610 enamide group Chemical group 0.000 title claims abstract description 22
150000001875 compounds Chemical class 0.000 title abstract description 27
238000000034 method Methods 0.000 title description 7
238000002360 preparation method Methods 0.000 title description 6
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 11
239000001257 hydrogen Substances 0.000 claims abstract description 11
150000003839 salts Chemical class 0.000 claims abstract description 10
229910052736 halogen Inorganic materials 0.000 claims abstract description 6
150000002367 halogens Chemical class 0.000 claims abstract description 6
CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 claims description 27
229960004397 cyclophosphamide Drugs 0.000 claims description 27
AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 claims description 24
239000000126 substance Substances 0.000 claims description 20
-1 acylated enamide compound Chemical class 0.000 claims description 12
230000000118 anti-neoplastic effect Effects 0.000 claims description 11
229960004679 doxorubicin Drugs 0.000 claims description 10
LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 claims description 8
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
125000004432 carbon atom Chemical group C* 0.000 claims description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
125000001931 aliphatic group Chemical group 0.000 claims description 5
150000001408 amides Chemical class 0.000 claims description 5
229940107700 pyruvic acid Drugs 0.000 claims description 4
229920006395 saturated elastomer Polymers 0.000 claims description 4
239000003242 anti bacterial agent Substances 0.000 claims description 3
229940088710 antibiotic agent Drugs 0.000 claims description 3
125000003118 aryl group Chemical group 0.000 claims description 3
229910052757 nitrogen Inorganic materials 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims 2
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
IDPURXSQCKYKIJ-UHFFFAOYSA-N 1-(4-methoxyphenyl)methanamine Chemical compound COC1=CC=C(CN)C=C1 IDPURXSQCKYKIJ-UHFFFAOYSA-N 0.000 claims 1
206010028980 Neoplasm Diseases 0.000 abstract description 20
238000011282 treatment Methods 0.000 abstract description 11
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125000000962 organic group Chemical group 0.000 abstract description 4
150000002431 hydrogen Chemical group 0.000 abstract description 2
241000699670 Mus sp. Species 0.000 description 24
239000000203 mixture Substances 0.000 description 21
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
241000700159 Rattus Species 0.000 description 15
201000011510 cancer Diseases 0.000 description 9
230000000694 effects Effects 0.000 description 8
208000032839 leukemia Diseases 0.000 description 8
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206010019695 Hepatic neoplasm Diseases 0.000 description 5
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239000003814 drug Substances 0.000 description 5
208000014018 liver neoplasm Diseases 0.000 description 5
239000002244 precipitate Substances 0.000 description 5
238000010992 reflux Methods 0.000 description 5
239000011734 sodium Substances 0.000 description 5
239000000243 solution Substances 0.000 description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
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 4
238000002347 injection Methods 0.000 description 4
239000007924 injection Substances 0.000 description 4
150000002500 ions Chemical class 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
108010090550 Benzopyrene Hydroxylase Proteins 0.000 description 3
108010015742 Cytochrome P-450 Enzyme System Proteins 0.000 description 3
102000002004 Cytochrome P-450 Enzyme System Human genes 0.000 description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
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238000001914 filtration Methods 0.000 description 3
230000003211 malignant effect Effects 0.000 description 3
238000002844 melting Methods 0.000 description 3
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125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
238000007911 parenteral administration Methods 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
231100000419 toxicity Toxicity 0.000 description 3
230000001988 toxicity Effects 0.000 description 3
230000001173 tumoral effect Effects 0.000 description 3
239000003981 vehicle Substances 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
STQGQHZAVUOBTE-UHFFFAOYSA-N 7-Cyan-hept-2t-en-4,6-diinsaeure Natural products C1=2C(O)=C3C(=O)C=4C(OC)=CC=CC=4C(=O)C3=C(O)C=2CC(O)(C(C)=O)CC1OC1CC(N)C(O)C(C)O1 STQGQHZAVUOBTE-UHFFFAOYSA-N 0.000 description 2
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
108010074633 Mixed Function Oxygenases Proteins 0.000 description 2
102000008109 Mixed Function Oxygenases Human genes 0.000 description 2
239000002253 acid Substances 0.000 description 2
239000004480 active ingredient Substances 0.000 description 2
229940009456 adriamycin Drugs 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
239000002775 capsule Substances 0.000 description 2
229960000975 daunorubicin Drugs 0.000 description 2
STQGQHZAVUOBTE-VGBVRHCVSA-N daunorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(C)=O)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 STQGQHZAVUOBTE-VGBVRHCVSA-N 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
229960002949 fluorouracil Drugs 0.000 description 2
238000011081 inoculation Methods 0.000 description 2
239000007927 intramuscular injection Substances 0.000 description 2
238000010255 intramuscular injection Methods 0.000 description 2
238000010253 intravenous injection Methods 0.000 description 2
239000007788 liquid Substances 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
238000013421 nuclear magnetic resonance imaging Methods 0.000 description 2
239000002674 ointment Substances 0.000 description 2
239000006187 pill Substances 0.000 description 2
239000000047 product Substances 0.000 description 2
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238000001228 spectrum Methods 0.000 description 2
239000003826 tablet Substances 0.000 description 2
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AGNGYMCLFWQVGX-AGFFZDDWSA-N (e)-1-[(2s)-2-amino-2-carboxyethoxy]-2-diazonioethenolate Chemical compound OC(=O)[C@@H](N)CO\C([O-])=C\[N+]#N AGNGYMCLFWQVGX-AGFFZDDWSA-N 0.000 description 1
206010003445 Ascites Diseases 0.000 description 1
102000015790 Asparaginase Human genes 0.000 description 1
108010024976 Asparaginase Proteins 0.000 description 1
108010006654 Bleomycin Proteins 0.000 description 1
COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
101100533230 Caenorhabditis elegans ser-2 gene Proteins 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical class [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
241000723375 Colchicum Species 0.000 description 1
241000518994 Conta Species 0.000 description 1
UHDGCWIWMRVCDJ-CCXZUQQUSA-N Cytarabine Chemical compound O=C1N=C(N)C=CN1[C@H]1[C@@H](O)[C@H](O)[C@@H](CO)O1 UHDGCWIWMRVCDJ-CCXZUQQUSA-N 0.000 description 1
108010092160 Dactinomycin Proteins 0.000 description 1
UQBOJOOOTLPNST-UHFFFAOYSA-N Dehydroalanine Chemical compound NC(=C)C(O)=O UQBOJOOOTLPNST-UHFFFAOYSA-N 0.000 description 1
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
102000004190 Enzymes Human genes 0.000 description 1
108090000790 Enzymes Proteins 0.000 description 1
239000001828 Gelatine Substances 0.000 description 1
ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 description 1
FBOZXECLQNJBKD-ZDUSSCGKSA-N L-methotrexate Chemical compound C=1N=C2N=C(N)N=C(N)C2=NC=1CN(C)C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 FBOZXECLQNJBKD-ZDUSSCGKSA-N 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
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical class [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
229930192392 Mitomycin Natural products 0.000 description 1
NWIBSHFKIJFRCO-WUDYKRTCSA-N Mytomycin Chemical compound C1N2C(C(C(C)=C(N)C3=O)=O)=C3[C@@H](COC(N)=O)[C@@]2(OC)[C@@H]2[C@H]1N2 NWIBSHFKIJFRCO-WUDYKRTCSA-N 0.000 description 1
108090000417 Oxygenases Proteins 0.000 description 1
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101100467517 Schizosaccharomyces pombe (strain 972 / ATCC 24843) raf2 gene Proteins 0.000 description 1
BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 1
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
239000005864 Sulphur Substances 0.000 description 1
241000863480 Vinca Species 0.000 description 1
230000009102 absorption Effects 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
RJURFGZVJUQBHK-IIXSONLDSA-N actinomycin D Chemical compound C[C@H]1OC(=O)[C@H](C(C)C)N(C)C(=O)CN(C)C(=O)[C@@H]2CCCN2C(=O)[C@@H](C(C)C)NC(=O)[C@H]1NC(=O)C1=C(N)C(=O)C(C)=C2OC(C(C)=CC=C3C(=O)N[C@@H]4C(=O)N[C@@H](C(N5CCC[C@H]5C(=O)N(C)CC(=O)N(C)[C@@H](C(C)C)C(=O)O[C@@H]4C)=O)C(C)C)=C3N=C21 RJURFGZVJUQBHK-IIXSONLDSA-N 0.000 description 1
239000013543 active substance Substances 0.000 description 1
239000000654 additive Substances 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
229930013930 alkaloid Natural products 0.000 description 1
229940100198 alkylating agent Drugs 0.000 description 1
239000002168 alkylating agent Substances 0.000 description 1
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230000001147 anti-toxic effect Effects 0.000 description 1
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239000007864 aqueous solution Substances 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
229960005070 ascorbic acid Drugs 0.000 description 1
235000010323 ascorbic acid Nutrition 0.000 description 1
239000011668 ascorbic acid Substances 0.000 description 1
229960003272 asparaginase Drugs 0.000 description 1
DCXYFEDJOCDNAF-UHFFFAOYSA-M asparaginate Chemical compound [O-]C(=O)C(N)CC(N)=O DCXYFEDJOCDNAF-UHFFFAOYSA-M 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
229950011321 azaserine Drugs 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
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OYVAGSVQBOHSSS-UAPAGMARSA-O bleomycin A2 Chemical compound N([C@H](C(=O)N[C@H](C)[C@@H](O)[C@H](C)C(=O)N[C@@H]([C@H](O)C)C(=O)NCCC=1SC=C(N=1)C=1SC=C(N=1)C(=O)NCCC[S+](C)C)[C@@H](O[C@H]1[C@H]([C@@H](O)[C@H](O)[C@H](CO)O1)O[C@@H]1[C@H]([C@@H](OC(N)=O)[C@H](O)[C@@H](CO)O1)O)C=1N=CNC=1)C(=O)C1=NC([C@H](CC(N)=O)NC[C@H](N)C(N)=O)=NC(N)=C1C OYVAGSVQBOHSSS-UAPAGMARSA-O 0.000 description 1
229960002092 busulfan Drugs 0.000 description 1
229910052791 calcium Chemical class 0.000 description 1
239000011575 calcium Chemical class 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
UFULAYFCSOUIOV-UHFFFAOYSA-N cysteamine Chemical compound NCCS UFULAYFCSOUIOV-UHFFFAOYSA-N 0.000 description 1
229960000684 cytarabine Drugs 0.000 description 1
239000000824 cytostatic agent Substances 0.000 description 1
230000001085 cytostatic effect Effects 0.000 description 1
229960000640 dactinomycin Drugs 0.000 description 1
229960001760 dimethyl sulfoxide Drugs 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
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229940088598 enzyme Drugs 0.000 description 1
239000000262 estrogen Substances 0.000 description 1
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239000003925 fat Substances 0.000 description 1
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210000004185 liver Anatomy 0.000 description 1
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239000006210 lotion Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
229960001924 melphalan Drugs 0.000 description 1
SGDBTWWWUNNDEQ-LBPRGKRZSA-N melphalan Chemical compound OC(=O)[C@@H](N)CC1=CC=C(N(CCCl)CCCl)C=C1 SGDBTWWWUNNDEQ-LBPRGKRZSA-N 0.000 description 1
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239000002184 metal Substances 0.000 description 1
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MXWHMTNPTTVWDM-NXOFHUPFSA-N mitoguazone Chemical compound NC(N)=N\N=C(/C)\C=N\N=C(N)N MXWHMTNPTTVWDM-NXOFHUPFSA-N 0.000 description 1
229960003539 mitoguazone Drugs 0.000 description 1
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239000002574 poison Substances 0.000 description 1
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XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
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238000005303 weighing Methods 0.000 description 1

Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CA000457455A 1984-06-26 1984-06-26 Composes d'enamide acyles, preparations pharmaceutiques les contenant, applications de ces preparations et procede de production Expired CA1249999A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000457455A CA1249999A (fr)	1984-06-26	1984-06-26	Composes d'enamide acyles, preparations pharmaceutiques les contenant, applications de ces preparations et procede de production

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA000457455A CA1249999A (fr)	1984-06-26	1984-06-26	Composes d'enamide acyles, preparations pharmaceutiques les contenant, applications de ces preparations et procede de production

Publications (1)

Publication Number	Publication Date
CA1249999A true CA1249999A (fr)	1989-02-14

Family

ID=4128174

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000457455A Expired CA1249999A (fr)	1984-06-26	1984-06-26	Composes d'enamide acyles, preparations pharmaceutiques les contenant, applications de ces preparations et procede de production

Country Status (1)

Country	Link
CA (1)	CA1249999A (fr)

1984
- 1984-06-26 CA CA000457455A patent/CA1249999A/fr not_active Expired

Legal Events

Date	Code	Title	Description
2006-02-14	MKEX	Expiry

Publication	Publication Date	Title
CA1302270C (fr)	1992-06-02	Agent carcinostatique
US5137918A (en)	1992-08-11	N-(2'-aminophenyl)-benzamide derivatives process for the preparation thereof and pharmaceutical compositions containing them
CY1201A (en)	1983-12-31	Substituted orthoanisamides methods of preparing them compositions containing them and their application as psychotropic agents
FI74705B (fi)	1987-11-30	Foerfarande foer framstaellning av nya kristallina bensotiazindioxidsalter.
US3666856A (en)	1972-05-30	Treating immune response with amino purine derivatives
US3758684A (en)	1973-09-11	Treating dna virus infections with amino purine derivatives
US4038416A (en)	1977-07-26	Pharmaceutical composition and method of the use thereof
US4066650A (en)	1978-01-03	Keto-aldehyde-amine addition products and method of making same
US4081534A (en)	1978-03-28	Amino purine nucleosides as autoimmune suppressant agents
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