CY1752A - 8a-Acylaminoergoline its preparation and pharmaceutical compositions containing it - Google Patents

8a-Acylaminoergoline its preparation and pharmaceutical compositions containing it Download PDF

Info

Publication number: CY1752A
Authority: CY; Cyprus
Prior art keywords: compound; formula; acid addition; addition salt; pharmaceutically acceptable
Prior art date: 1987-06-23

Application number

CY175294A

Other languages

English (en)

Original Assignee

Sandoz 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.)

1987-06-23

Filing date

1994-06-03

Publication date

1994-06-03

1994-06-03 Application filed by Sandoz Ltd filed Critical Sandoz Ltd

1994-06-03 Publication of CY1752A publication Critical patent/CY1752A/en

Links

239000008194 pharmaceutical composition Substances 0.000 title claims description 9
238000002360 preparation method Methods 0.000 title description 3
150000001875 compounds Chemical class 0.000 claims description 62
150000003839 salts Chemical class 0.000 claims description 27
239000002253 acid Substances 0.000 claims description 23
239000012458 free base Substances 0.000 claims description 11
238000000034 method Methods 0.000 claims description 10
FWWOWPGPERBCNJ-UHFFFAOYSA-N 2-hydroxy-4-(2-hydroxyethoxy)-4-oxobutanoic acid Chemical compound OCCOC(=O)CC(O)C(O)=O FWWOWPGPERBCNJ-UHFFFAOYSA-N 0.000 claims description 7
238000004519 manufacturing process Methods 0.000 claims description 7
208000028017 Psychotic disease Diseases 0.000 claims description 5
230000000701 neuroleptic effect Effects 0.000 claims description 5
208000018737 Parkinson disease Diseases 0.000 claims description 4
230000000648 anti-parkinson Effects 0.000 claims description 3
239000000939 antiparkinson agent Substances 0.000 claims description 3
239000003176 neuroleptic agent Substances 0.000 claims description 3
239000003937 drug carrier Substances 0.000 claims description 2
239000008024 pharmaceutical diluent Substances 0.000 claims description 2
241000700159 Rattus Species 0.000 description 14
102000003946 Prolactin Human genes 0.000 description 12
108010057464 Prolactin Proteins 0.000 description 12
229940097325 prolactin Drugs 0.000 description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
238000012360 testing method Methods 0.000 description 11
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
230000000694 effects Effects 0.000 description 8
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 7
229960004046 apomorphine Drugs 0.000 description 7
VMWNQDUVQKEIOC-CYBMUJFWSA-N apomorphine Chemical compound C([C@H]1N(C)CC2)C3=CC=C(O)C(O)=C3C3=C1C2=CC=C3 VMWNQDUVQKEIOC-CYBMUJFWSA-N 0.000 description 7
239000002775 capsule Substances 0.000 description 7
229940079593 drug Drugs 0.000 description 7
239000003814 drug Substances 0.000 description 7
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 7
210000002966 serum Anatomy 0.000 description 7
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
230000035929 gnawing Effects 0.000 description 6
239000000243 solution Substances 0.000 description 6
241001465754 Metazoa Species 0.000 description 5
239000000872 buffer Substances 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 4
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 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
235000019441 ethanol Nutrition 0.000 description 4
238000002474 experimental method Methods 0.000 description 4
239000004615 ingredient Substances 0.000 description 4
239000008101 lactose Substances 0.000 description 4
235000019359 magnesium stearate Nutrition 0.000 description 4
229940057948 magnesium stearate Drugs 0.000 description 4
239000008188 pellet Substances 0.000 description 4
230000000144 pharmacologic effect Effects 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-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
229920002472 Starch Polymers 0.000 description 3
238000003556 assay Methods 0.000 description 3
239000002585 base Substances 0.000 description 3
230000027455 binding Effects 0.000 description 3
238000007796 conventional method Methods 0.000 description 3
230000002401 inhibitory effect Effects 0.000 description 3
229940102223 injectable solution Drugs 0.000 description 3
230000005923 long-lasting effect Effects 0.000 description 3
239000012528 membrane Substances 0.000 description 3
-1 methyl- Chemical group 0.000 description 3
239000000203 mixture Substances 0.000 description 3
238000000159 protein binding assay Methods 0.000 description 3
102000005962 receptors Human genes 0.000 description 3
108020003175 receptors Proteins 0.000 description 3
239000011780 sodium chloride Substances 0.000 description 3
229950001675 spiperone Drugs 0.000 description 3
239000008107 starch Substances 0.000 description 3
235000019698 starch Nutrition 0.000 description 3
238000007920 subcutaneous administration Methods 0.000 description 3
239000000725 suspension Substances 0.000 description 3
RKZACOKFBAFYPQ-PSOPSSQASA-N (6ar,9s,10ar)-5,7-dimethyl-6,6a,8,9,10,10a-hexahydro-4h-indolo[4,3-fg]quinoline-9-amine Chemical compound C1=CC([C@H]2C[C@H](N)CN([C@@H]2C2)C)=C3C2=C(C)NC3=C1 RKZACOKFBAFYPQ-PSOPSSQASA-N 0.000 description 2
PAQZWJGSJMLPMG-UHFFFAOYSA-N 2,4,6-tripropyl-1,3,5,2$l^{5},4$l^{5},6$l^{5}-trioxatriphosphinane 2,4,6-trioxide Chemical compound CCCP1(=O)OP(=O)(CCC)OP(=O)(CCC)O1 PAQZWJGSJMLPMG-UHFFFAOYSA-N 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
208000009132 Catalepsy Diseases 0.000 description 2
229920002261 Corn starch Polymers 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
206010022998 Irritability Diseases 0.000 description 2
WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
206010047853 Waxy flexibility Diseases 0.000 description 2
239000013543 active substance Substances 0.000 description 2
150000001266 acyl halides Chemical class 0.000 description 2
OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
244000309466 calf Species 0.000 description 2
239000001913 cellulose Substances 0.000 description 2
229920002678 cellulose Polymers 0.000 description 2
239000008120 corn starch Substances 0.000 description 2
VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 2
239000003136 dopamine receptor stimulating agent Substances 0.000 description 2
239000002552 dosage form Substances 0.000 description 2
230000002124 endocrine Effects 0.000 description 2
LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 2
239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 2
235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 2
229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 2
UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 2
JBFYUZGYRGXSFL-UHFFFAOYSA-N imidazolide Chemical compound C1=C[N-]C=N1 JBFYUZGYRGXSFL-UHFFFAOYSA-N 0.000 description 2
239000012442 inert solvent Substances 0.000 description 2
230000003902 lesion Effects 0.000 description 2
239000003446 ligand Substances 0.000 description 2
238000005567 liquid scintillation counting Methods 0.000 description 2
238000005259 measurement Methods 0.000 description 2
230000009871 nonspecific binding Effects 0.000 description 2
230000003389 potentiating effect Effects 0.000 description 2
238000003127 radioimmunoassay Methods 0.000 description 2
201000000980 schizophrenia Diseases 0.000 description 2
230000028327 secretion Effects 0.000 description 2
239000012439 solid excipient Substances 0.000 description 2
238000012453 sprague-dawley rat model Methods 0.000 description 2
GOTMKOSCLKVOGG-OAHLLOKOSA-N (5R)-8-chloro-3-methyl-5-phenyl-1,2,4,5-tetrahydro-3-benzazepin-7-ol Chemical compound C1([C@@H]2C3=CC(O)=C(Cl)C=C3CCN(C2)C)=CC=CC=C1 GOTMKOSCLKVOGG-OAHLLOKOSA-N 0.000 description 1
SKYZYDSNJIOXRL-BTQNPOSSSA-N (6ar)-6-methyl-5,6,6a,7-tetrahydro-4h-dibenzo[de,g]quinoline-10,11-diol;hydrochloride Chemical compound Cl.C([C@H]1N(C)CC2)C3=CC=C(O)C(O)=C3C3=C1C2=CC=C3 SKYZYDSNJIOXRL-BTQNPOSSSA-N 0.000 description 1
IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
XNAQEDQKXCHDIW-UHFFFAOYSA-N 2-ethyl-2-methylbutanoyl chloride Chemical compound CCC(C)(CC)C(Cl)=O XNAQEDQKXCHDIW-UHFFFAOYSA-N 0.000 description 1
102000056834 5-HT2 Serotonin Receptors Human genes 0.000 description 1
108091005479 5-HT2 receptors Proteins 0.000 description 1
229910002012 Aerosil® Inorganic materials 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
208000031872 Body Remains Diseases 0.000 description 1
FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
206010012289 Dementia Diseases 0.000 description 1
102000015554 Dopamine receptor Human genes 0.000 description 1
108050004812 Dopamine receptor Proteins 0.000 description 1
239000004150 EU approved colour Substances 0.000 description 1
208000001287 Galactorrhea Diseases 0.000 description 1
206010017600 Galactorrhoea Diseases 0.000 description 1
239000001828 Gelatine Substances 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
239000004425 Makrolon Substances 0.000 description 1
229930195725 Mannitol Natural products 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
238000011672 OFA rat Methods 0.000 description 1
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
206010033864 Paranoia Diseases 0.000 description 1
208000027099 Paranoid disease Diseases 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
240000008042 Zea mays Species 0.000 description 1
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
235000002017 Zea mays subsp mays Nutrition 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
150000001263 acyl chlorides Chemical class 0.000 description 1
235000010443 alginic acid Nutrition 0.000 description 1
239000000783 alginic acid Substances 0.000 description 1
229920000615 alginic acid Polymers 0.000 description 1
229960001126 alginic acid Drugs 0.000 description 1
150000004781 alginic acids Chemical class 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
230000003042 antagnostic effect Effects 0.000 description 1
229960003990 apomorphine hydrochloride Drugs 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
239000008280 blood Substances 0.000 description 1
230000037396 body weight Effects 0.000 description 1
210000004556 brain Anatomy 0.000 description 1
210000005013 brain tissue Anatomy 0.000 description 1
CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
229940078456 calcium stearate Drugs 0.000 description 1
239000008116 calcium stearate Substances 0.000 description 1
235000013539 calcium stearate Nutrition 0.000 description 1
229910002092 carbon dioxide Inorganic materials 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 1
239000001768 carboxy methyl cellulose Substances 0.000 description 1
239000004359 castor oil Substances 0.000 description 1
235000019438 castor oil Nutrition 0.000 description 1
230000001484 cataleptigenic effect Effects 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
RSUVYMGADVXGOU-BUHFOSPRSA-N cinanserin Chemical compound CN(C)CCCSC1=CC=CC=C1NC(=O)\C=C\C1=CC=CC=C1 RSUVYMGADVXGOU-BUHFOSPRSA-N 0.000 description 1
229950001684 cinanserin Drugs 0.000 description 1
238000004040 coloring Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
235000005822 corn Nutrition 0.000 description 1
229960000913 crospovidone Drugs 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000007423 decrease Effects 0.000 description 1
238000006073 displacement reaction Methods 0.000 description 1
229960003638 dopamine Drugs 0.000 description 1
230000007368 endocrine function Effects 0.000 description 1
230000001747 exhibiting effect Effects 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
235000013305 food Nutrition 0.000 description 1
235000003599 food sweetener Nutrition 0.000 description 1
210000001035 gastrointestinal tract Anatomy 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
239000008187 granular material Substances 0.000 description 1
201000000079 gynecomastia Diseases 0.000 description 1
229960003878 haloperidol Drugs 0.000 description 1
229940088597 hormone Drugs 0.000 description 1
239000005556 hormone Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
230000001771 impaired effect Effects 0.000 description 1
230000001939 inductive effect Effects 0.000 description 1
239000003701 inert diluent Substances 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
238000012417 linear regression Methods 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
230000001592 luteinising effect Effects 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
239000012457 nonaqueous media Substances 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
239000003921 oil Substances 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
DIVDFFZHCJEHGG-UHFFFAOYSA-N oxidopamine Chemical compound NCCC1=CC(O)=C(O)C=C1O DIVDFFZHCJEHGG-UHFFFAOYSA-N 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
229940068196 placebo Drugs 0.000 description 1
239000000902 placebo Substances 0.000 description 1
239000004033 plastic Substances 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
229920000515 polycarbonate Polymers 0.000 description 1
235000013809 polyvinylpolypyrrolidone Nutrition 0.000 description 1
229920000523 polyvinylpolypyrrolidone Polymers 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
229940069328 povidone Drugs 0.000 description 1
208000020016 psychiatric disease Diseases 0.000 description 1
238000010992 reflux Methods 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000000661 sodium alginate Substances 0.000 description 1
235000010413 sodium alginate Nutrition 0.000 description 1
229940005550 sodium alginate Drugs 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
230000009870 specific binding Effects 0.000 description 1
229940032147 starch Drugs 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
229960004274 stearic acid Drugs 0.000 description 1
230000004936 stimulating effect Effects 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
210000003523 substantia nigra Anatomy 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
230000002459 sustained effect Effects 0.000 description 1
239000012730 sustained-release form Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
230000015883 synaptic transmission, dopaminergic Effects 0.000 description 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
238000010998 test method Methods 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
238000003828 vacuum filtration Methods 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
239000008215 water for injection Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D457/00—Heterocyclic compounds containing indolo [4, 3-f, g] quinoline ring systems, e.g. derivatives of ergoline, of the formula:, e.g. lysergic acid
- C07D457/10—Heterocyclic compounds containing indolo [4, 3-f, g] quinoline ring systems, e.g. derivatives of ergoline, of the formula:, e.g. lysergic acid with hetero atoms directly attached in position 8
- C07D457/12—Nitrogen atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/48—Ergoline derivatives, e.g. lysergic acid, ergotamine
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Medicinal Chemistry (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Neurology (AREA)
Chemical Kinetics & Catalysis (AREA)
Biomedical Technology (AREA)
Neurosurgery (AREA)
Anesthesiology (AREA)
Psychiatry (AREA)
Epidemiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Hydrogenated Pyridines (AREA)

CY175294A 1987-06-23 1994-06-03 8a-Acylaminoergoline its preparation and pharmaceutical compositions containing it CY1752A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE3720656		1987-06-23

Publications (1)

Publication Number	Publication Date
CY1752A true CY1752A (en)	1994-06-03

Family

ID=6330087

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CY175294A CY1752A (en)	1987-06-23	1994-06-03	8a-Acylaminoergoline its preparation and pharmaceutical compositions containing it

Country Status (28)

Country	Link
US (1)	US5075318A (de)
JP (1)	JPH0670052B2 (de)
KR (1)	KR970001527B1 (de)
AT (1)	AT395242B (de)
AU (1)	AU615657B2 (de)
BE (1)	BE1004034A3 (de)
CA (1)	CA1302404C (de)
CH (1)	CH674646A5 (de)
CY (1)	CY1752A (de)
DK (1)	DK169335B1 (de)
ES (1)	ES2010282A6 (de)
FI (1)	FI88302C (de)
FR (1)	FR2617166B1 (de)
GB (1)	GB2206115B (de)
GR (1)	GR1002318B (de)
HK (1)	HK2794A (de)
HU (2)	HU203097B (de)
IE (1)	IE60550B1 (de)
IL (1)	IL86820A (de)
IT (1)	IT1219652B (de)
LU (1)	LU87251A1 (de)
MY (1)	MY103584A (de)
NL (1)	NL8801597A (de)
NZ (1)	NZ225112A (de)
PH (1)	PH24690A (de)
PT (1)	PT87781B (de)
SE (1)	SE467925B (de)
ZA (1)	ZA884505B (de)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CH664568A5 (de) *	1984-01-12	1988-03-15	Sandoz Ag	8-alpha-acylaminoergoline.
JP3630888B2 (ja) *	1996-10-31	2005-03-23	株式会社ニデック	レンズ搬送装置と眼鏡レンズを搬送するための眼鏡レンズ用固定カップ及びレンズ搬送方法
JP6265583B2 (ja)	2008-10-17	2018-01-24	ウィスコンシンアルムニリサーチファンデイション	生理活性アルファベータペプチドを作製する方法

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CH664568A5 (de) *	1984-01-12	1988-03-15	Sandoz Ag	8-alpha-acylaminoergoline.
HU195810B (en) *	1984-12-24	1988-07-28	Sandoz Ag	Process for preparing new 8alpha-acyl-amino-ergoline derivatives and pharmaceutical compositions containing such compounds

1988
- 1988-06-17 IT IT48097/88A patent/IT1219652B/it active
- 1988-06-20 LU LU87251A patent/LU87251A1/fr unknown
- 1988-06-20 GB GB8814615A patent/GB2206115B/en not_active Expired - Lifetime
- 1988-06-20 FR FR888808357A patent/FR2617166B1/fr not_active Expired - Lifetime
- 1988-06-20 BE BE8800702A patent/BE1004034A3/fr not_active IP Right Cessation
- 1988-06-21 DK DK340188A patent/DK169335B1/da not_active IP Right Cessation
- 1988-06-21 PT PT87781A patent/PT87781B/pt not_active IP Right Cessation
- 1988-06-21 IL IL86820A patent/IL86820A/xx not_active IP Right Cessation
- 1988-06-21 GR GR880100401A patent/GR1002318B/el unknown
- 1988-06-21 CH CH2387/88A patent/CH674646A5/de not_active IP Right Cessation
- 1988-06-21 HU HU883159A patent/HU203097B/hu not_active IP Right Cessation
- 1988-06-21 MY MYPI88000682A patent/MY103584A/en unknown
- 1988-06-21 NZ NZ225112A patent/NZ225112A/en unknown
- 1988-06-21 SE SE8802323A patent/SE467925B/sv not_active IP Right Cessation
- 1988-06-21 IE IE186788A patent/IE60550B1/en not_active IP Right Cessation
- 1988-06-21 AU AU18194/88A patent/AU615657B2/en not_active Ceased
- 1988-06-22 AT AT0161788A patent/AT395242B/de not_active IP Right Cessation
- 1988-06-22 JP JP63154570A patent/JPH0670052B2/ja not_active Expired - Lifetime
- 1988-06-22 PH PH37103A patent/PH24690A/en unknown
- 1988-06-22 FI FI883008A patent/FI88302C/fi not_active IP Right Cessation
- 1988-06-22 KR KR1019880007511A patent/KR970001527B1/ko not_active Expired - Fee Related
- 1988-06-22 CA CA000570102A patent/CA1302404C/en not_active Expired - Lifetime
- 1988-06-23 ES ES8801948A patent/ES2010282A6/es not_active Expired
- 1988-06-23 NL NL8801597A patent/NL8801597A/nl active Search and Examination
- 1988-06-23 ZA ZA884505A patent/ZA884505B/xx unknown
1990
- 1990-11-02 US US07/608,454 patent/US5075318A/en not_active Expired - Lifetime
1994
- 1994-01-13 HK HK27/94A patent/HK2794A/xx not_active IP Right Cessation
- 1994-06-03 CY CY175294A patent/CY1752A/en unknown
1995
- 1995-06-15 HU HU95P/P00209P patent/HU211651A9/hu unknown

Also Published As

Publication number	Publication date
FI883008A0 (fi)	1988-06-22
JPH0670052B2 (ja)	1994-09-07
KR970001527B1 (ko)	1997-02-11
CA1302404C (en)	1992-06-02
SE8802323L (sv)	1988-12-24
FR2617166B1 (fr)	1992-07-17
HU211651A9 (en)	1995-12-28
ATA161788A (de)	1992-03-15
IL86820A (en)	1991-07-18
US5075318A (en)	1991-12-24
GB2206115B (en)	1991-04-03
FI88302B (fi)	1993-01-15
IT8848097A0 (it)	1988-06-17
ZA884505B (en)	1990-02-28
MY103584A (en)	1993-08-28
IE881867L (en)	1988-12-23
PH24690A (en)	1990-09-07
GR880100401A (el)	1989-03-08
GB2206115A (en)	1988-12-29
GR1002318B (el)	1996-05-13
GB8814615D0 (en)	1988-07-27
PT87781A (pt)	1989-05-31
AU1819488A (en)	1989-01-05
AU615657B2 (en)	1991-10-10
AT395242B (de)	1992-10-27
JPS6422876A (en)	1989-01-25
FI883008L (fi)	1988-12-24
FR2617166A1 (fr)	1988-12-30
NZ225112A (en)	1991-03-26
BE1004034A3 (fr)	1992-09-15
LU87251A1 (fr)	1989-03-08
IE60550B1 (en)	1994-07-27
PT87781B (pt)	1992-10-30
DK340188D0 (da)	1988-06-21
HUT50174A (en)	1989-12-28
NL8801597A (nl)	1989-01-16
ES2010282A6 (es)	1989-11-01
IL86820A0 (en)	1988-11-30
CH674646A5 (de)	1990-06-29
HU203097B (en)	1991-05-28
IT1219652B (it)	1990-05-24
SE8802323D0 (sv)	1988-06-21
FI88302C (fi)	1993-04-26
KR890000479A (ko)	1989-03-14
HK2794A (en)	1994-01-21
DK340188A (da)	1988-12-24
DK169335B1 (da)	1994-10-10
SE467925B (sv)	1992-10-05

Publication	Publication Date	Title
HU211575A9 (en)	1995-12-28	2-methyl-thieno-benzodiazepine
IE68434B1 (en)	1996-06-12	New tricyclic compounds
NO327896B1 (no)	2009-10-12	Tricykliske benzodiazepiner, farmasoytisk sammensetning, anvendelse av forbindelsene samt mellomprodukter som er nyttige ved syntese av forbindelsene
DK156001B (da)	1989-06-12	Analogifremgangsmaade til fremstilling af mercaptosubstituerede 2,3,4,5-tetrahydro-1h-3-benzazepiner
GB2071095A (en)	1981-09-16	Heterocyclic compounds processes for their preparation and pharmaceutical compositions containing them
EP0200455B1 (de)	1991-01-30	5-substituierte 2,3,4,5-Tetrahydro-1H-3-benzazepine
FI97806C (fi)	1997-02-25	Menetelmä terapeuttisesti aktiivisten dihydrobentsofuraanikarboksamidien valmistamiseksi
CS247094B2 (en)	1986-11-13	Preparation method of 5,11-dihydro-11-(((methyl-4-piperidinyl)amino)carbonyl)-6h-dibenz(b,e)-azepin-6-on
US5075318A (en)	1991-12-24	8α-acylaminoergoline, its preparation and pharmaceutical compositions containing it
JPH08507498A (ja)	1996-08-13	複素環式化合物、それらの使用および製法
US5637596A (en)	1997-06-10	Azabicycloalkyl derivatives of imidazo[1,5-a]indol-3-one and process for their preparation
US4424225A (en)	1984-01-03	Thienobenzodiazepinones, pharmaceutical compositions thereof and method of use thereof
DK162050B (da)	1991-09-09	Pyrazolderivater med ergolinskelet eller salte deraf, deres fremstilling, farmaceutiske praeparater indeholdende disse og fremgangsmaade til fremstilling af de farmaceutiske praeparater
US4032640A (en)	1977-06-28	4H-Benzo[4,5]cyclohepta[1,2-b]thiophenes
HU201759B (en)	1990-12-28	Process for producing new condensed diazepinones and pharmaceutical compositions comprising same
US4410527A (en)	1983-10-18	Substituted thienobenzodiazepinones and salts thereof
US4673674A (en)	1987-06-16	Diazepinoindoles useful for treating depression, schizophrenia, social withdrawal or anxiety and pharmaceutical compositions containing them
HU206214B (en)	1992-09-28	Process for producing pyrido/63,4-b//1,4/benzoxazepine derivatives and pharmaceutical compositions comprising same
NZ203216A (en)	1985-09-13	Pyridobenzodiazepinone derivatives and pharmaceutical compositions
RU2043991C1 (ru)	1995-09-20	Дигидробензофурановые карбоксамиды или его фармацевтически приемлемые соли и способ их получения
NZ203194A (en)	1985-09-13	Dibenzodiazepinone derivatives and pharmaceutical compositions
DK157925B (da)	1990-03-05	2,3,4,5-tetrahydro-1h-3-benzazepinderivater og farmaceutiske praeparater indeholdende disse
PL157529B1 (en)	1992-06-30	Method for manufacturing 8 alfa-acyloaminergoline