NO753197L - - Google Patents

Info

Publication number: NO753197L
Authority: NO; Norway
Prior art keywords: formula; acid; compound; compounds; dihydro
Prior art date: 1974-09-27

Application number

NO753197A

Other languages

English (en)

Norwegian (no)

Inventor

P Stadler

H Depoortere

Original Assignee

Sandoz Ag

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.)

1974-09-27

Filing date

1975-09-19

Publication date

1976-03-30

1975-09-19 Application filed by Sandoz Ag filed Critical Sandoz Ag

1976-03-30 Publication of NO753197L publication Critical patent/NO753197L/no

Links

150000001875 compounds Chemical class 0.000 claims description 26
239000002253 acid Substances 0.000 claims description 22
238000000034 method Methods 0.000 claims description 18
239000003054 catalyst Substances 0.000 claims description 9
150000003839 salts Chemical class 0.000 claims description 9
125000000217 alkyl group Chemical group 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 4
125000004432 carbon atom Chemical group C* 0.000 claims description 3
150000002391 heterocyclic compounds Chemical class 0.000 claims description 2
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 30
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 13
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
238000002844 melting Methods 0.000 description 11
230000008018 melting Effects 0.000 description 11
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
238000005984 hydrogenation reaction Methods 0.000 description 8
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
229910052763 palladium Inorganic materials 0.000 description 6
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
150000001408 amides Chemical class 0.000 description 5
150000001540 azides Chemical class 0.000 description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
239000013078 crystal Substances 0.000 description 4
238000000354 decomposition reaction Methods 0.000 description 4
150000002148 esters Chemical class 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
239000002904 solvent Substances 0.000 description 4
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
-1 alkyl radical Chemical class 0.000 description 3
FSIZNIXUPRQTLZ-QMTHXVAHSA-N lysergic acid Chemical class C1=CC=C2C3=C[C@@H](C(O)=O)CN(C)[C@@H]3CC3=CN=C1[C]32 FSIZNIXUPRQTLZ-QMTHXVAHSA-N 0.000 description 3
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
239000000047 product Substances 0.000 description 3
125000006239 protecting group Chemical group 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
ZAGRKAFMISFKIO-UHFFFAOYSA-N Isolysergic acid Natural products C1=CC(C2=CC(CN(C2C2)C)C(O)=O)=C3C2=CNC3=C1 ZAGRKAFMISFKIO-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
150000007933 aliphatic carboxylic acids Chemical class 0.000 description 2
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
239000012320 chlorinating reagent Substances 0.000 description 2
238000003776 cleavage reaction Methods 0.000 description 2
235000019441 ethanol Nutrition 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
238000007327 hydrogenolysis reaction Methods 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
239000000203 mixture Substances 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
230000000803 paradoxical effect Effects 0.000 description 2
239000008363 phosphate buffer Substances 0.000 description 2
230000007017 scission Effects 0.000 description 2
239000007858 starting material Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 2
230000007306 turnover Effects 0.000 description 2
DNXIKVLOVZVMQF-UHFFFAOYSA-N (3beta,16beta,17alpha,18beta,20alpha)-17-hydroxy-11-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-yohimban-16-carboxylic acid, methyl ester Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(O)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 DNXIKVLOVZVMQF-UHFFFAOYSA-N 0.000 description 1
ORBSYPFBZQJNJE-MPKXVKKWSA-N (6ar,9r,10ar)-7-methyl-6,6a,8,9,10,10a-hexahydro-4h-indolo[4,3-fg]quinoline-9-carboxylic acid Chemical class C1=CC([C@H]2C[C@H](CN([C@@H]2C2)C)C(O)=O)=C3C2=CNC3=C1 ORBSYPFBZQJNJE-MPKXVKKWSA-N 0.000 description 1
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-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
NAMYKGVDVNBCFQ-UHFFFAOYSA-N 2-bromopropane Chemical compound CC(C)Br NAMYKGVDVNBCFQ-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
241000282326 Felis catus Species 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
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 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
241000700159 Rattus Species 0.000 description 1
LCQMZZCPPSWADO-UHFFFAOYSA-N Reserpilin Natural products COC(=O)C1COCC2CN3CCc4c([nH]c5cc(OC)c(OC)cc45)C3CC12 LCQMZZCPPSWADO-UHFFFAOYSA-N 0.000 description 1
QEVHRUUCFGRFIF-SFWBKIHZSA-N Reserpine Natural products O=C(OC)[C@@H]1[C@H](OC)[C@H](OC(=O)c2cc(OC)c(OC)c(OC)c2)C[C@H]2[C@@H]1C[C@H]1N(C2)CCc2c3c([nH]c12)cc(OC)cc3 QEVHRUUCFGRFIF-SFWBKIHZSA-N 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
229930013930 alkaloid Natural products 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000000969 carrier Substances 0.000 description 1
230000002490 cerebral effect Effects 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical compound OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
238000006482 condensation reaction Methods 0.000 description 1
WBKFWQBXFREOFH-UHFFFAOYSA-N dichloromethane;ethyl acetate Chemical compound ClCCl.CCOC(C)=O WBKFWQBXFREOFH-UHFFFAOYSA-N 0.000 description 1
239000003814 drug Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
RHGUXDUPXYFCTE-ZWNOBZJWSA-N ergoline Chemical class C1=CC([C@@H]2[C@H](NCCC2)C2)=C3C2=CNC3=C1 RHGUXDUPXYFCTE-ZWNOBZJWSA-N 0.000 description 1
230000000763 evoking effect Effects 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000006260 foam Substances 0.000 description 1
125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000000463 material Substances 0.000 description 1
229940126601 medicinal product Drugs 0.000 description 1
239000000155 melt Substances 0.000 description 1
ORIBUSCBDFDAIQ-GYYYEOQOSA-N methyl (6ar,9r)-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxylate Chemical compound C1=CC(C2[C@H](NC[C@@H](C2)C(=O)OC)C2)=C3C2=CNC3=C1 ORIBUSCBDFDAIQ-GYYYEOQOSA-N 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
229910000510 noble metal Inorganic materials 0.000 description 1
150000007530 organic bases Chemical group 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
239000003791 organic solvent mixture Substances 0.000 description 1
PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
230000003285 pharmacodynamic effect Effects 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
108090000765 processed proteins & peptides Proteins 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
BJOIZNZVOZKDIG-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC(OC)=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 BJOIZNZVOZKDIG-MDEJGZGSSA-N 0.000 description 1
229960003147 reserpine Drugs 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 1
238000007127 saponification reaction Methods 0.000 description 1
238000004904 shortening Methods 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
230000002618 waking effect Effects 0.000 description 1
238000005406 washing Methods 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
- C07D519/02—Ergot alkaloids of the cyclic peptide type

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

NO753197A 1974-09-27 1975-09-19 NO753197L (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH1308774A CH602765A5 (de)	1974-09-27	1974-09-27

Publications (1)

Publication Number	Publication Date
NO753197L true NO753197L (de)	1976-03-30

Family

ID=4389176

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO753197A NO753197L (de)	1974-09-27	1975-09-19

Country Status (16)

Country	Link
JP (1)	JPS5168599A (de)
AU (1)	AU506218B2 (de)
BE (1)	BE833835A (de)
CH (1)	CH602765A5 (de)
DD (1)	DD122532A5 (de)
DE (1)	DE2541426A1 (de)
DK (1)	DK420375A (de)
ES (1)	ES441257A1 (de)
FI (1)	FI752616A (de)
FR (1)	FR2285885A1 (de)
GB (1)	GB1519505A (de)
IL (1)	IL48179A (de)
NL (1)	NL7511178A (de)
NO (1)	NO753197L (de)
SE (1)	SE7510552L (de)
ZA (1)	ZA756129B (de)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
YU40275B (en) *	1976-03-04	1985-12-31	Lek Tovarna Farmacevtskih	Process for preparing 9,10-dihydro-ergosine and physiologically tolerated acid addition salts thereof
CH649300A5 (de) *	1981-08-07	1985-05-15	Sandoz Ag	Ergopeptinderivate, ihre herstellung und verwendung.
BE895842A (fr) *	1982-02-12	1983-08-08	Sandoz Sa	Nouveaux alcaloides ergopeptidiques, leur preparation et leur utilisation comme medicaments
DE3303616A1 (de) *	1982-02-12	1983-08-25	Sandoz-Patent-GmbH, 7850 Lörrach	Mutterkornalkaloide, verfahren zu deren herstellung sowie diese verbindungen enthaltende pharmazeutische zubereitungen

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3314959A (en) *	1961-05-10	1967-04-18	Sandoz Ltd	Intermediates for the synthesis of ergot alkaloids
CH505102A (de) *	1967-11-01	1971-03-31	Sandoz Ag	Verfahren zur Herstellung neuer Mutterkornpeptidalkaloide

1974
- 1974-09-27 CH CH1308774A patent/CH602765A5/xx not_active IP Right Cessation
1975
- 1975-09-17 DE DE19752541426 patent/DE2541426A1/de not_active Withdrawn
- 1975-09-18 DK DK420375A patent/DK420375A/da unknown
- 1975-09-19 FI FI752616A patent/FI752616A/fi not_active Application Discontinuation
- 1975-09-19 SE SE7510552A patent/SE7510552L/xx unknown
- 1975-09-19 NO NO753197A patent/NO753197L/no unknown
- 1975-09-23 NL NL7511178A patent/NL7511178A/xx not_active Application Discontinuation
- 1975-09-24 GB GB39092/75A patent/GB1519505A/en not_active Expired
- 1975-09-25 IL IL48179A patent/IL48179A/xx unknown
- 1975-09-25 BE BE160393A patent/BE833835A/xx unknown
- 1975-09-25 DD DD188562A patent/DD122532A5/xx unknown
- 1975-09-25 ES ES441257A patent/ES441257A1/es not_active Expired
- 1975-09-25 AU AU85200/75A patent/AU506218B2/en not_active Expired
- 1975-09-26 ZA ZA756129A patent/ZA756129B/xx unknown
- 1975-09-26 JP JP50115696A patent/JPS5168599A/ja active Pending
- 1975-09-26 FR FR7529491A patent/FR2285885A1/fr active Granted

Also Published As

Publication number	Publication date
DE2541426A1 (de)	1976-04-15
SE7510552L (sv)	1976-03-29
AU8520075A (en)	1977-03-31
IL48179A0 (en)	1975-11-25
IL48179A (en)	1978-06-15
BE833835A (fr)	1976-03-25
DD122532A5 (de)	1976-10-12
ES441257A1 (es)	1977-07-01
GB1519505A (en)	1978-07-26
NL7511178A (nl)	1976-03-30
FR2285885B1 (de)	1979-09-14
AU506218B2 (en)	1979-12-20
ZA756129B (en)	1977-04-27
JPS5168599A (de)	1976-06-14
CH602765A5 (de)	1978-07-31
FI752616A (de)	1976-03-28
FR2285885A1 (fr)	1976-04-23
DK420375A (da)	1976-03-28

Publication	Publication Date	Title
EP0399814A2 (de)	1990-11-28	Phenol-Derivate zur Beschleunigung des Wachstumsfaktors menschlicher Nerven
NO753197L (de)	1976-03-30
AU612000B2 (en)	1991-06-27	A process for the preparation of pyrrolidone derivatives
NO744175L (de)	1975-06-23
US4247704A (en)	1981-01-27	Hexahydro thieno imadazole intermediates for the synthesis of biotin
HU218274B (en)	2000-07-28	N,n'-bis hydroxyalkyl and alkoxyalkyl-pyridine-2,4-dicarboxylic acid diamide derivatives and pharmaceutical compositions comprising such compounds and process for producing them
KR100324040B1 (ko)	2002-07-22	합성적 용도로 사용하기 위한 신규한 중간체 및아미노피페라진유도체를제조하는방법
US2970147A (en)	1961-01-31	3-hydroxy-nu-(heterocyclic-ethyl)-morphinans
US4005090A (en)	1977-01-25	8-(β-AMINOETHYL)ERGOLINES-I
SU1650007A3 (ru)	1991-05-15	Способ получени 1-[3-меркапто-(2S)-метилпропионил]-пирролидин-(2S)-карбоновой кислоты
SU786902A3 (ru)	1980-12-07	Способ получени 6-амино-2,3,5,6-тетрагидро-спиро /пенам-2,4-(4н)(тио)пиран/-3карбоновой кислоты или ее сложного эфира
US4563464A (en)	1986-01-07	2-Azabicyclo(2.2.2)octane derivatives and their use as immunosuppressive agents
KR940002828B1 (ko)	1994-04-04	2-옥소-1-옥사-8-아자스피로(Azaspiro)[4,5]데칸 유도체와 그 제조방법
DE3915950A1 (de)	1990-11-15	8(alpha)-acylamino-ergoline, ihre herstellung und verwendung als arzneimittel
Shaw et al.	1957	Indole Carboxamidines and Aminomethylindoles as Antimetabolites of Serotonin
US4284557A (en)	1981-08-18	Intermediate racemates for the preparation of biotin and a process for their preparation
US4320056A (en)	1982-03-16	Certain thia-diazatricyclo[3,3,3,08,11 ]tridecanes, and their preparation
SE460969B (sv)	1989-12-11	Apovincaminsyraderivat, foerfarande foer framstaellning daerav och farmaceutiska kompositioner innehaallande dessa derivat
KR920010074B1 (ko)	1992-11-13	에르골린 유도체의 제조방법
KR20010030637A (ko)	2001-04-16	아미노피페라진 유도체의 신규한 제조방법
US6355804B1 (en)	2002-03-12	Process for producing piperidinecarboxylic acid amide derivatives
NO154635B (no)	1986-08-11	Fremgangsmaate for fremstilling av terapeutisk aktive ergotalkaloider.
US4382031A (en)	1983-05-03	Intermediates for the preparation of biotin
GB1593410A (en)	1981-07-15	N-substituted-6,7-dialkoxy-1,2,3,4-tetrahydro-1-isoquinoline acetamides
US5929240A (en)	1999-07-27	Process and intermediates for preparing naphthyridonecarboxylic acid salts