CH626897A5 - - Google Patents

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Info

Publication number: CH626897A5
Authority: CH; Switzerland
Prior art keywords: coenzyme; derivatives; prepared; dimethylbenzimidazolyl; water
Prior art date: 1976-11-25

Application number

CH1448677A

Other languages

English (en)

French (fr)

Inventor

Denise Autissier

Pierre Barthelemy

Original Assignee

Roussel Uclaf

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.)

1976-11-25

Filing date

1977-11-25

Publication date

1981-12-15

1977-11-25 Application filed by Roussel Uclaf filed Critical Roussel Uclaf

1981-03-30 Priority to CH215281A priority Critical patent/CH628640A5/fr

1981-12-15 Publication of CH626897A5 publication Critical patent/CH626897A5/fr

Links

-1 5,6-dimethyl-benzimidazolyl Chemical group 0.000 claims description 19
238000000034 method Methods 0.000 claims description 16
239000011789 cobamamide Substances 0.000 claims description 15
235000006279 cobamamide Nutrition 0.000 claims description 14
ZIHHMGTYZOSFRC-UWWAPWIJSA-M cobamamide Chemical compound C1(/[C@](C)(CCC(=O)NC[C@H](C)OP(O)(=O)OC2[C@H]([C@H](O[C@@H]2CO)N2C3=CC(C)=C(C)C=C3N=C2)O)[C@@H](CC(N)=O)[C@]2(N1[Co+]C[C@@H]1[C@H]([C@@H](O)[C@@H](O1)N1C3=NC=NC(N)=C3N=C1)O)[H])=C(C)\C([C@H](C/1(C)C)CCC(N)=O)=N\C\1=C/C([C@H]([C@@]\1(CC(N)=O)C)CCC(N)=O)=N/C/1=C(C)\C1=N[C@]2(C)[C@@](C)(CC(N)=O)[C@@H]1CCC(N)=O ZIHHMGTYZOSFRC-UWWAPWIJSA-M 0.000 claims description 14
OAJLVMGLJZXSGX-SLAFOUTOSA-L (2s,3s,4r,5r)-2-(6-aminopurin-9-yl)-5-methanidyloxolane-3,4-diol;cobalt(3+);[(2r,3s,4r,5s)-5-(5,6-dimethylbenzimidazol-1-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl] [(2r)-1-[3-[(1r,2r,3r,4z,7s,9z,12s,13s,14z,17s,18s,19r)-2,13,18-tris(2-amino-2-oxoethyl)-7 Chemical class [Co+3].O[C@H]1[C@@H](O)[C@@H]([CH2-])O[C@@H]1N1C2=NC=NC(N)=C2N=C1.[N-]([C@@H]1[C@H](CC(N)=O)[C@@]2(C)CCC(=O)NC[C@@H](C)OP([O-])(=O)O[C@H]3[C@H]([C@H](O[C@@H]3CO)N3C4=CC(C)=C(C)C=C4N=C3)O)\C2=C(C)/C([C@H](C\2(C)C)CCC(N)=O)=N/C/2=C\C([C@H]([C@@]/2(CC(N)=O)C)CCC(N)=O)=N\C\2=C(C)/C2=N[C@]1(C)[C@@](C)(CC(N)=O)[C@@H]2CCC(N)=O OAJLVMGLJZXSGX-SLAFOUTOSA-L 0.000 claims description 13
125000004432 carbon atom Chemical group C* 0.000 claims description 8
238000002360 preparation method Methods 0.000 claims description 6
239000005515 coenzyme Substances 0.000 claims description 5
239000002253 acid Substances 0.000 claims description 4
239000003795 chemical substances by application Substances 0.000 claims description 3
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 33
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
239000008346 aqueous phase Substances 0.000 description 20
239000000243 solution Substances 0.000 description 20
239000000203 mixture Substances 0.000 description 18
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 12
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 11
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
239000012074 organic phase Substances 0.000 description 10
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
238000003756 stirring Methods 0.000 description 8
239000007864 aqueous solution Substances 0.000 description 7
239000003814 drug Substances 0.000 description 7
239000000284 extract Substances 0.000 description 6
239000012071 phase Substances 0.000 description 6
VKEQBMCRQDSRET-UHFFFAOYSA-N Methylone Chemical compound CNC(C)C(=O)C1=CC=C2OCOC2=C1 VKEQBMCRQDSRET-UHFFFAOYSA-N 0.000 description 5
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
239000000047 product Substances 0.000 description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
229930003779 Vitamin B12 Natural products 0.000 description 4
FDJOLVPMNUYSCM-WZHZPDAFSA-L cobalt(3+);[(2r,3s,4r,5s)-5-(5,6-dimethylbenzimidazol-1-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl] [(2r)-1-[3-[(1r,2r,3r,4z,7s,9z,12s,13s,14z,17s,18s,19r)-2,13,18-tris(2-amino-2-oxoethyl)-7,12,17-tris(3-amino-3-oxopropyl)-3,5,8,8,13,15,18,19-octamethyl-2 Chemical compound [Co+3].N#[C-].N([C@@H]([C@]1(C)[N-]\C([C@H]([C@@]1(CC(N)=O)C)CCC(N)=O)=C(\C)/C1=N/C([C@H]([C@@]1(CC(N)=O)C)CCC(N)=O)=C\C1=N\C([C@H](C1(C)C)CCC(N)=O)=C/1C)[C@@H]2CC(N)=O)=C\1[C@]2(C)CCC(=O)NC[C@@H](C)OP([O-])(=O)O[C@H]1[C@@H](O)[C@@H](N2C3=CC(C)=C(C)C=C3N=C2)O[C@@H]1CO FDJOLVPMNUYSCM-WZHZPDAFSA-L 0.000 description 4
229940079593 drug Drugs 0.000 description 4
239000008194 pharmaceutical composition Substances 0.000 description 4
235000019163 vitamin B12 Nutrition 0.000 description 4
239000011715 vitamin B12 Substances 0.000 description 4
230000036765 blood level Effects 0.000 description 3
239000000843 powder Substances 0.000 description 3
238000000746 purification Methods 0.000 description 3
UNSAJINGUOTTRA-UHFFFAOYSA-N 3-(3-bromophenyl)prop-2-yn-1-ol Chemical compound OCC#CC1=CC=CC(Br)=C1 UNSAJINGUOTTRA-UHFFFAOYSA-N 0.000 description 2
KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
206010003549 asthenia Diseases 0.000 description 2
239000002775 capsule Substances 0.000 description 2
239000012153 distilled water Substances 0.000 description 2
238000001035 drying Methods 0.000 description 2
ARBOVOVUTSQWSS-UHFFFAOYSA-N hexadecanoyl chloride Chemical compound CCCCCCCCCCCCCCCC(Cl)=O ARBOVOVUTSQWSS-UHFFFAOYSA-N 0.000 description 2
PKHMTIRCAFTBDS-UHFFFAOYSA-N hexanoyl hexanoate Chemical compound CCCCCC(=O)OC(=O)CCCCC PKHMTIRCAFTBDS-UHFFFAOYSA-N 0.000 description 2
210000005229 liver cell Anatomy 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
238000012986 modification Methods 0.000 description 2
230000004048 modification Effects 0.000 description 2
WTBAHSZERDXKKZ-UHFFFAOYSA-N octadecanoyl chloride Chemical compound CCCCCCCCCCCCCCCCCC(Cl)=O WTBAHSZERDXKKZ-UHFFFAOYSA-N 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
102000004169 proteins and genes Human genes 0.000 description 2
108090000623 proteins and genes Proteins 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
239000000126 substance Substances 0.000 description 2
235000013343 vitamin Nutrition 0.000 description 2
239000011782 vitamin Substances 0.000 description 2
229930003231 vitamin Natural products 0.000 description 2
229940088594 vitamin Drugs 0.000 description 2
150000003722 vitamin derivatives Chemical class 0.000 description 2
YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 description 1
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
206010053759 Growth retardation Diseases 0.000 description 1
229920000084 Gum arabic Polymers 0.000 description 1
241000282412 Homo Species 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
102000004895 Lipoproteins Human genes 0.000 description 1
108090001030 Lipoproteins Proteins 0.000 description 1
208000002720 Malnutrition Diseases 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
102000011931 Nucleoproteins Human genes 0.000 description 1
108010061100 Nucleoproteins Proteins 0.000 description 1
208000025747 Rheumatic disease Diseases 0.000 description 1
241000978776 Senegalia senegal Species 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
208000014306 Trophic disease Diseases 0.000 description 1
239000000205 acacia gum Substances 0.000 description 1
235000010489 acacia gum Nutrition 0.000 description 1
150000008065 acid anhydrides Chemical class 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
238000013019 agitation Methods 0.000 description 1
125000005907 alkyl ester group Chemical group 0.000 description 1
230000001195 anabolic effect Effects 0.000 description 1
230000000202 analgesic effect Effects 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
208000022531 anorexia Diseases 0.000 description 1
239000008135 aqueous vehicle Substances 0.000 description 1
230000003851 biochemical process Effects 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000008280 blood Substances 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
206010061428 decreased appetite Diseases 0.000 description 1
230000002950 deficient Effects 0.000 description 1
230000001079 digestive effect Effects 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
238000006911 enzymatic reaction Methods 0.000 description 1
238000004108 freeze drying Methods 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
239000008187 granular material Substances 0.000 description 1
231100000001 growth retardation Toxicity 0.000 description 1
238000010255 intramuscular injection Methods 0.000 description 1
239000007927 intramuscular injection Substances 0.000 description 1
239000008101 lactose Substances 0.000 description 1
230000002045 lasting effect Effects 0.000 description 1
125000000400 lauroyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000007788 liquid Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
230000003340 mental effect Effects 0.000 description 1
125000001419 myristoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000002687 nonaqueous vehicle Substances 0.000 description 1
125000002801 octanoyl group Chemical group C(CCCCCCC)(=O)* 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
125000001312 palmitoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
230000000552 rheumatic effect Effects 0.000 description 1
UIIMBOGNXHQVGW-UHFFFAOYSA-M sodium bicarbonate Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
125000003696 stearoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000000112 undernutrition Nutrition 0.000 description 1
125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
230000004580 weight loss Effects 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H23/00—Compounds containing boron, silicon or a metal, e.g. chelates or vitamin B12
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/02—Nutrients, e.g. vitamins, minerals

Landscapes

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

CH1448677A 1976-11-25 1977-11-25 CH626897A5 (de)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CH215281A CH628640A5 (en)	1977-11-25	1981-03-30	Acyl derivatives of coenzyme B12

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
FR7635533A FR2373285A1 (fr)	1976-11-25	1976-11-25	Nouveaux derives du coenzyme b 12, procede de preparation et application a titre de medicaments de ces nouveaux produits

Publications (1)

Publication Number	Publication Date
CH626897A5 true CH626897A5 (de)	1981-12-15

Family

ID=9180307

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1448677A CH626897A5 (de)	1976-11-25	1977-11-25

Country Status (13)

Country	Link
US (1)	US4364939A (de)
JP (1)	JPS5365900A (de)
AR (1)	AR214651A1 (de)
BE (1)	BE861159A (de)
CH (1)	CH626897A5 (de)
DE (1)	DE2752756A1 (de)
DK (1)	DK521177A (de)
ES (1)	ES463682A1 (de)
FR (1)	FR2373285A1 (de)
GB (1)	GB1549930A (de)
MX (1)	MX4325E (de)
NL (1)	NL7712953A (de)
PT (1)	PT67322B (de)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NZ217821A (en) *	1985-10-10	1989-07-27	Biotech Australia Pty Ltd	Oral delivery system; complex of active agent and vitamin b12 or analogue thereof
US5807832A (en) *	1987-06-09	1998-09-15	Biotech Australia Pty Limited	Oral delivery of biologically active substances bound to vitamin B12
US4925931A (en) *	1988-07-14	1990-05-15	Mccully Kilmer S	N-homocysteine thiolactonyl retinamido cobalamin and methods of use thereof
US5405839A (en) *	1989-02-28	1995-04-11	Teijin Limited	Vitamin B12 derivative, preparation process thereof, and use thereof
WO1990010014A1 (fr) *	1989-02-28	1990-09-07	Teijin Limited	Nouveau derive de vitamine b12, sa production et son application
CA2084194C (en) *	1991-04-02	2003-05-20	Gregory John Russell-Jones	Oral delivery systems for microparticles
DE19943167A1 (de) *	1999-09-09	2001-03-15	Elenac Gmbh	Verfahren zur Herstellung von geträgerten Chromkatalysatoren

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NL111024C (de) *	1958-07-10	1900-01-01
US3151116A (en) *	1961-11-03	1964-09-29	Ciba Geigy Corp	Certain 2-aza-indolo [2, 3-alpha] quinolizine compounds
GB963373A (en) *	1961-12-11	1964-07-08	Glaxo Group Ltd	Improvements in or relating to substituted cobamides
FR1450375A (fr) *	1961-12-11	1966-06-24	Glaxo Group Ltd	Procédé de préparation d'un co-enzyme de vitamine b12 et d'analogues de celui-ci
DE1670941A1 (de) *	1967-10-14	1971-02-25	Bayer Ag	Alkylsulfonylcobalamine

1976
- 1976-11-25 FR FR7635533A patent/FR2373285A1/fr active Granted
1977
- 1977-10-28 ES ES463682A patent/ES463682A1/es not_active Expired
- 1977-11-02 AR AR269820A patent/AR214651A1/es active
- 1977-11-23 GB GB48739/77A patent/GB1549930A/en not_active Expired
- 1977-11-24 BE BE182900A patent/BE861159A/xx not_active IP Right Cessation
- 1977-11-24 NL NL7712953A patent/NL7712953A/xx unknown
- 1977-11-24 DK DK521177A patent/DK521177A/da not_active Application Discontinuation
- 1977-11-24 MX MX776577U patent/MX4325E/es unknown
- 1977-11-24 PT PT67322A patent/PT67322B/pt unknown
- 1977-11-25 DE DE19772752756 patent/DE2752756A1/de not_active Ceased
- 1977-11-25 CH CH1448677A patent/CH626897A5/fr not_active IP Right Cessation
- 1977-11-25 JP JP14081577A patent/JPS5365900A/ja active Pending
1980
- 1980-09-15 US US06/186,831 patent/US4364939A/en not_active Expired - Lifetime

Also Published As

Publication number	Publication date
JPS5365900A (en)	1978-06-12
BE861159A (fr)	1978-05-24
US4364939A (en)	1982-12-21
PT67322A (fr)	1977-12-01
GB1549930A (en)	1979-08-08
PT67322B (fr)	1979-10-10
FR2373285B1 (de)	1979-03-30
DE2752756A1 (de)	1978-06-01
FR2373285A1 (fr)	1978-07-07
AR214651A1 (es)	1979-07-13
MX4325E (es)	1982-03-24
ES463682A1 (es)	1978-07-01
NL7712953A (nl)	1978-05-29
DK521177A (da)	1978-05-26

Legal Events

Date	Code	Title	Description
1987-07-31	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
EP0318377B1 (de)	1993-08-25	Enantiomere Derivate von Aminosäure, Verfahren zu deren Herstellung und deren therapeutische Verwendung
CH655936A5 (fr)	1986-05-30	Derives du 3-amino pregn-5-ene, leurs sels, leur preparation, medicaments et compositions les renfermant.
LU83795A1 (fr)	1983-09-01	Xanthates,leur preparation et leur utilisation
CH626897A5 (de)	1981-12-15
EP0046113A1 (de)	1982-02-17	Peptide und ihre Anwendung in der Therapeutik
FR2510112A1 (fr)	1983-01-28	Nouveaux derives du 2-oxo-pyrid-3-yl ou piperidin-3-yl indole, leurs sels, procede de preparation, application a titre de medicaments et compositions les renfermant
BE897843A (fr)	1984-01-16	Derives biologiquement actifs de 2, 5-piperazinediones, procede pour leur preparation et compositions pharmaceutique en contenant
CH616943A5 (de)	1980-04-30
FR2510583A1 (fr)	1983-02-04	Derives nouveaux d'acide ursodesoxycholique, leur procede de preparation et leur application en therapeutique
EP0316322A1 (de)	1989-05-24	Tetrapeptid-hemmstoff zum eintritt in den kreislauf von hemopoietischen stammzellen, verfahren zu deren herstellung und deren anwendungen.
CH627648A5 (fr)	1982-01-29	Nouveaux derives de 20,21-dinoreburnamenine, procede de preparation et compositions pharmaceutiques.
EP0001021B1 (de)	1981-09-16	Derivate pentacyclischer Alkaloide, Verfahren zu deren Herstellung, Anwendung für die Synthese von Produkten der Eburnamoningruppe und pharmazeutische Zusammensetzungen
CH628640A5 (en)	1982-03-15	Acyl derivatives of coenzyme B12
FR2507477A1 (fr)	1982-12-17	Nouveau procede de preparation d'un extrait de feuilles d'olea europea riche en oleuropeine, produits obtenus, application a titre de medicaments et compositions les renfermant
CH675998A5 (de)	1990-11-30
EP0052028A1 (de)	1982-05-19	Hexapeptide, deren Herstellung, deren Anwendung in Arzneimitteln und sie enthaltende Zusammensetzungen
LU83822A1 (fr)	1983-09-01	Derives n-(vinblastinoyl-23)d'acides amines,leur preparation et leur application therapeutique
CA1140155A (fr)	1983-01-25	PROCEDE DE PREPARATION D'UN NOUVEAU DERIVE DU 1.alpha.,25-DIHYDROXY CHOLECALCIFEROL
CH653332A5 (fr)	1985-12-31	Derives du tetrahydropyridin-4-yl indole et leurs sels, leur preparation et les medicaments les renfermant.
CH640529A5 (fr)	1984-01-13	Procede de preparation d'un acide chromone carboxylique.
CA1140111A (fr)	1983-01-25	PROCEDE DE PREPARATION D'UN NOUVEAU DERIVE DU (20S) 3.alpha.- /(AMINO-ACETYL)AMINO/ 5.alpha.-PREGNAN-20-OL ET DE SES SELS
CH642961A5 (fr)	1984-05-15	Beta-lactones derivees de l'acide 2-hydroxy cyclopentane carboxylique, leurs procedes de preparation et les compositions pharmaceutiques les renfermant.
EP0300107A1 (de)	1989-01-25	Ester, Thioester und Amid-Derivate von Oxolinsäure, Verfahren zu ihrer Herstellung und ihre therapeutische Verwendung
EP0315519B1 (de)	1993-03-24	Aminopimelinsäure-Derivate, Verfahren zu deren Herstellung und deren Verwendung als Arzneimittel
EP0449722B1 (de)	1994-10-19	Neue Komplexe der Tiaprofensäure oder ihrer unlöslichen oder zum Teil löslichen Ester mit den Cyclodextrinen oder ihren Derivaten