JPH0147478B2 - - Google Patents

Info

Publication number: JPH0147478B2
Authority: JP; Japan
Prior art keywords: hydrogen; compound; methyl; alkyl; formula
Prior art date: 1979-06-12
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

JP55079575A

Other languages

English (en)

Japanese (ja)

Other versions

JPS562992A (en

Inventor

Borigaa Jooji

Sutochu Peetaa

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.)

Sandoz AG

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.)

1979-06-12

Filing date

1980-06-11

Publication date

1989-10-13

1980-06-11 Application filed by Sandoz AG filed Critical Sandoz AG

1981-01-13 Publication of JPS562992A publication Critical patent/JPS562992A/ja

1989-10-13 Publication of JPH0147478B2 publication Critical patent/JPH0147478B2/ja

Status Granted legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 claims description 125
229910052739 hydrogen Inorganic materials 0.000 claims description 56
239000001257 hydrogen Substances 0.000 claims description 56
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 43
125000000217 alkyl group Chemical group 0.000 claims description 32
239000002253 acid Substances 0.000 claims description 22
238000000034 method Methods 0.000 claims description 21
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 18
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 18
229910052794 bromium Inorganic materials 0.000 claims description 18
150000003839 salts Chemical class 0.000 claims description 17
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 16
150000002431 hydrogen Chemical class 0.000 claims description 13
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
229960004704 dihydroergotamine Drugs 0.000 claims description 9
239000012458 free base Substances 0.000 claims description 7
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 7
230000028327 secretion Effects 0.000 claims description 6
102000003946 Prolactin Human genes 0.000 claims description 5
108010057464 Prolactin Proteins 0.000 claims description 5
238000004519 manufacturing process Methods 0.000 claims description 5
229940097325 prolactin Drugs 0.000 claims description 5
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
239000004480 active ingredient Substances 0.000 claims description 4
239000000939 antiparkinson agent Substances 0.000 claims description 4
125000004432 carbon atom Chemical group C* 0.000 claims description 4
238000009833 condensation Methods 0.000 claims description 4
230000005494 condensation Effects 0.000 claims description 4
230000000648 anti-parkinson Effects 0.000 claims description 3
239000000935 antidepressant agent Substances 0.000 claims description 3
229940005513 antidepressants Drugs 0.000 claims description 3
239000003814 drug Substances 0.000 claims description 3
208000019695 Migraine disease Diseases 0.000 claims description 2
230000001430 anti-depressive effect Effects 0.000 claims description 2
230000037007 arousal Effects 0.000 claims description 2
229960004290 dihydroergocornine Drugs 0.000 claims description 2
229960004318 dihydroergocristine Drugs 0.000 claims description 2
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 2
208000035475 disorder Diseases 0.000 claims description 2
239000003623 enhancer Substances 0.000 claims description 2
229960004943 ergotamine Drugs 0.000 claims description 2
239000003112 inhibitor Substances 0.000 claims description 2
206010027599 migraine Diseases 0.000 claims description 2
230000002746 orthostatic effect Effects 0.000 claims description 2
230000001263 anti-prolactin effect Effects 0.000 claims 1
229950010031 beta-ergocryptine Drugs 0.000 claims 1
AFFLEALSHYGOOD-NOURLPFCSA-N mergocriptine Chemical compound C1=CC(C=2[C@H](N(C)C[C@@H](C=2)C(=O)N[C@]2(C(=O)N3[C@H](C(N4CCC[C@H]4[C@]3(O)O2)=O)CC(C)C)C(C)C)C2)=C3C2=C(C)NC3=C1 AFFLEALSHYGOOD-NOURLPFCSA-N 0.000 claims 1
229940124597 therapeutic agent Drugs 0.000 claims 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 72
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 51
241001465754 Metazoa Species 0.000 description 21
238000002844 melting Methods 0.000 description 21
230000008018 melting Effects 0.000 description 21
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
239000000203 mixture Substances 0.000 description 18
238000000354 decomposition reaction Methods 0.000 description 16
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
230000000694 effects Effects 0.000 description 15
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
238000012360 testing method Methods 0.000 description 13
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 12
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
239000000243 solution Substances 0.000 description 12
238000002425 crystallisation Methods 0.000 description 11
230000008025 crystallization Effects 0.000 description 11
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
230000002378 acidificating effect Effects 0.000 description 10
238000006243 chemical reaction Methods 0.000 description 10
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
241000700159 Rattus Species 0.000 description 9
229940126062 Compound A Drugs 0.000 description 8
NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 8
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 7
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
229930015720 peptide alkaloid Natural products 0.000 description 6
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
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 5
LCQMZZCPPSWADO-UHFFFAOYSA-N Reserpilin Natural products COC(=O)C1COCC2CN3CCc4c([nH]c5cc(OC)c(OC)cc45)C3CC12 LCQMZZCPPSWADO-UHFFFAOYSA-N 0.000 description 5
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 5
YDOTUXAWKBPQJW-UHFFFAOYSA-N alpha-Ergocryptinine Natural products C1=CC(C=2C(N(C)CC(C=2)C(=O)NC2(C(=O)N3C(C(N4CCCC4C3(O)O2)=O)CC(C)C)C(C)C)C2)=C3C2=CNC3=C1 YDOTUXAWKBPQJW-UHFFFAOYSA-N 0.000 description 5
239000003054 catalyst Substances 0.000 description 5
238000007796 conventional method Methods 0.000 description 5
238000011156 evaluation Methods 0.000 description 5
238000002474 experimental method Methods 0.000 description 5
238000002513 implantation Methods 0.000 description 5
239000007788 liquid Substances 0.000 description 5
230000000144 pharmacologic effect Effects 0.000 description 5
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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 5
229960003147 reserpine Drugs 0.000 description 5
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 5
229910000029 sodium carbonate Inorganic materials 0.000 description 5
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 5
239000002841 Lewis acid Substances 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-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
239000002552 dosage form Substances 0.000 description 4
239000003937 drug carrier Substances 0.000 description 4
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
150000007517 lewis acids Chemical class 0.000 description 4
-1 lithium aluminum hydride Chemical compound 0.000 description 4
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
239000012044 organic layer Substances 0.000 description 4
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
239000000741 silica gel Substances 0.000 description 4
229910002027 silica gel Inorganic materials 0.000 description 4
239000002904 solvent Substances 0.000 description 4
239000007858 starting material Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
239000003826 tablet Substances 0.000 description 4
VPVIYKRQVDIGOH-UHFFFAOYSA-N 2-chloro-1,3-dithiane Chemical compound ClC1SCCCS1 VPVIYKRQVDIGOH-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 3
241000282326 Felis catus Species 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
239000007868 Raney catalyst Substances 0.000 description 3
229910000564 Raney nickel Inorganic materials 0.000 description 3
229920002472 Starch Polymers 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
150000001408 amides Chemical class 0.000 description 3
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 3
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239000001530 fumaric acid Substances 0.000 description 3
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DIVDFFZHCJEHGG-UHFFFAOYSA-N oxidopamine Chemical compound NCCC1=CC(O)=C(O)C=C1O DIVDFFZHCJEHGG-UHFFFAOYSA-N 0.000 description 3
WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 3
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238000007920 subcutaneous administration Methods 0.000 description 3
239000000454 talc Substances 0.000 description 3
235000012222 talc Nutrition 0.000 description 3
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XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
238000010626 work up procedure Methods 0.000 description 3
ZCQPDHIMSLIIDW-MEBBXXQBSA-N (6ar,9r)-5,7-dimethyl-6,6a,8,9-tetrahydro-4h-indolo[4,3-fg]quinoline-9-carboxylic acid Chemical class C1=CC(C2=C[C@H](CN([C@@H]2C2)C)C(O)=O)=C3C2=C(C)NC3=C1 ZCQPDHIMSLIIDW-MEBBXXQBSA-N 0.000 description 2
HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 2
KRXAVBPUAIKSFF-UHFFFAOYSA-N 3,4-dihydrodithiine Chemical compound C1CC=CSS1 KRXAVBPUAIKSFF-UHFFFAOYSA-N 0.000 description 2
AWFDCTXCTHGORH-HGHGUNKESA-N 6-[4-[(6ar,9r,10ar)-5-bromo-7-methyl-6,6a,8,9,10,10a-hexahydro-4h-indolo[4,3-fg]quinoline-9-carbonyl]piperazin-1-yl]-1-methylpyridin-2-one Chemical class O=C([C@H]1CN([C@H]2[C@@H](C=3C=CC=C4NC(Br)=C(C=34)C2)C1)C)N(CC1)CCN1C1=CC=CC(=O)N1C AWFDCTXCTHGORH-HGHGUNKESA-N 0.000 description 2
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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
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150000008064 anhydrides Chemical class 0.000 description 2
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QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
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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
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
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JQZWMPJGACUNFN-UHFFFAOYSA-N 2-chloro-1,3-dithiolane Chemical compound ClC1SCCS1 JQZWMPJGACUNFN-UHFFFAOYSA-N 0.000 description 1
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QLMRJHFAGVFUAC-UHFFFAOYSA-N 5-(2-aminoethyl)benzene-1,2,4-triol;hydron;chloride Chemical compound Cl.NCCC1=CC(O)=C(O)C=C1O QLMRJHFAGVFUAC-UHFFFAOYSA-N 0.000 description 1
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ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical class [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
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102000001189 Cyclic Peptides Human genes 0.000 description 1
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229920000084 Gum arabic Polymers 0.000 description 1
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 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical group CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
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238000011672 OFA rat Methods 0.000 description 1
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RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical class [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
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238000010521 absorption reaction Methods 0.000 description 1
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150000004781 alginic acids Chemical class 0.000 description 1
150000003797 alkaloid derivatives Chemical group 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
YDOTUXAWKBPQJW-NSLWYYNWSA-N alpha-ergocryptine Chemical compound C1=CC(C=2[C@H](N(C)C[C@@H](C=2)C(=O)N[C@]2(C(=O)N3[C@H](C(N4CCC[C@H]4[C@]3(O)O2)=O)CC(C)C)C(C)C)C2)=C3C2=CNC3=C1 YDOTUXAWKBPQJW-NSLWYYNWSA-N 0.000 description 1
235000012211 aluminium silicate Nutrition 0.000 description 1
125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 1
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230000003078 antioxidant effect Effects 0.000 description 1
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QDWJUBJKEHXSMT-UHFFFAOYSA-N boranylidynenickel Chemical group [Ni]#B QDWJUBJKEHXSMT-UHFFFAOYSA-N 0.000 description 1
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235000010216 calcium carbonate Nutrition 0.000 description 1
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238000001035 drying Methods 0.000 description 1
239000003480 eluent Substances 0.000 description 1
238000010828 elution Methods 0.000 description 1
238000006345 epimerization reaction Methods 0.000 description 1
235000010228 ethyl p-hydroxybenzoate Nutrition 0.000 description 1
NUVBSKCKDOMJSU-UHFFFAOYSA-N ethylparaben Chemical class CCOC(=O)C1=CC=C(O)C=C1 NUVBSKCKDOMJSU-UHFFFAOYSA-N 0.000 description 1
238000000605 extraction Methods 0.000 description 1
210000001105 femoral artery Anatomy 0.000 description 1
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210000003754 fetus Anatomy 0.000 description 1
ONKJLIUSEXIAKL-QUDADGMASA-N garamine Chemical compound O1C[C@@](O)(C)[C@H](NC)[C@@H](O)[C@H]1O[C@@H]1[C@@H](O)[C@H](O)[C@@H](N)C[C@H]1N ONKJLIUSEXIAKL-QUDADGMASA-N 0.000 description 1
210000001035 gastrointestinal tract Anatomy 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
XLSMFKSTNGKWQX-UHFFFAOYSA-N hydroxyacetone Chemical compound CC(=O)CO XLSMFKSTNGKWQX-UHFFFAOYSA-N 0.000 description 1
230000009610 hypersensitivity Effects 0.000 description 1
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238000007912 intraperitoneal administration Methods 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
238000010253 intravenous injection Methods 0.000 description 1
238000006317 isomerization reaction Methods 0.000 description 1
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
239000010410 layer Substances 0.000 description 1
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239000012280 lithium aluminium hydride Substances 0.000 description 1
230000007774 longterm Effects 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
ZAGRKAFMISFKIO-QMTHXVAHSA-N lysergic acid Chemical compound C1=CC(C2=C[C@H](CN([C@@H]2C2)C)C(O)=O)=C3C2=CNC3=C1 ZAGRKAFMISFKIO-QMTHXVAHSA-N 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
150000002688 maleic acid derivatives Chemical class 0.000 description 1
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238000005399 mechanical ventilation Methods 0.000 description 1
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229920000609 methyl cellulose Polymers 0.000 description 1
230000011987 methylation Effects 0.000 description 1
238000007069 methylation reaction Methods 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
229960002900 methylcellulose Drugs 0.000 description 1
235000010981 methylcellulose Nutrition 0.000 description 1
235000013336 milk Nutrition 0.000 description 1
239000008267 milk Substances 0.000 description 1
210000004080 milk Anatomy 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
229940105631 nembutal Drugs 0.000 description 1
QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 description 1
239000003921 oil Substances 0.000 description 1
230000000803 paradoxical effect Effects 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
229960001412 pentobarbital Drugs 0.000 description 1
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239000004033 plastic Substances 0.000 description 1
239000003880 polar aprotic solvent Substances 0.000 description 1
239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
229920000053 polysorbate 80 Polymers 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
230000026234 pro-estrus Effects 0.000 description 1
239000000047 product Substances 0.000 description 1
239000003586 protic polar solvent Substances 0.000 description 1
201000003004 ptosis Diseases 0.000 description 1
238000011084 recovery Methods 0.000 description 1
230000001850 reproductive effect Effects 0.000 description 1
102220004588 rs104893797 Human genes 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
238000012216 screening Methods 0.000 description 1
210000003625 skull Anatomy 0.000 description 1
235000010413 sodium alginate Nutrition 0.000 description 1
239000000661 sodium alginate Substances 0.000 description 1
229940005550 sodium alginate Drugs 0.000 description 1
235000017550 sodium carbonate Nutrition 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
239000000829 suppository Substances 0.000 description 1
230000001629 suppression Effects 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
239000012730 sustained-release form Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
238000010189 synthetic method Methods 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000006188 syrup Substances 0.000 description 1
239000007916 tablet composition Substances 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
238000010998 test method Methods 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
210000001519 tissue Anatomy 0.000 description 1
239000010936 titanium Chemical class 0.000 description 1
229910052719 titanium Inorganic materials 0.000 description 1
YONPGGFAJWQGJC-UHFFFAOYSA-K titanium(iii) chloride Chemical compound Cl[Ti](Cl)Cl YONPGGFAJWQGJC-UHFFFAOYSA-K 0.000 description 1
210000003437 trachea Anatomy 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
238000007039 two-step reaction Methods 0.000 description 1
210000004291 uterus Anatomy 0.000 description 1
230000003639 vasoconstrictive effect Effects 0.000 description 1
238000009423 ventilation Methods 0.000 description 1
239000001993 wax Substances 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
239000011701 zinc Chemical class 0.000 description 1
229910052725 zinc Inorganic materials 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
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
- 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
- A61P25/24—Antidepressants
- 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
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Engineering & Computer Science (AREA)
Chemical Kinetics & Catalysis (AREA)
Veterinary Medicine (AREA)
Medicinal Chemistry (AREA)
Bioinformatics & Cheminformatics (AREA)
Public Health (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Pain & Pain Management (AREA)
Psychiatry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

JP7957580A 1979-06-12 1980-06-11 Ergot peptide derivative* its manufacture and drug composition containing it Granted JPS562992A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH547679A CH642082A5 (en)	1979-06-12	1979-06-12	Ergopeptin derivatives, their preparation and use

Publications (2)

Publication Number	Publication Date
JPS562992A JPS562992A (en)	1981-01-13
JPH0147478B2 true JPH0147478B2 (fr)	1989-10-13

Family

ID=4294236

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP7957580A Granted JPS562992A (en)	1979-06-12	1980-06-11	Ergot peptide derivative* its manufacture and drug composition containing it

Country Status (4)

Country	Link
JP (1)	JPS562992A (fr)
BE (1)	BE883711A (fr)
CH (1)	CH642082A5 (fr)
ZA (1)	ZA803516B (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
KR20140042868A (ko) *	2011-06-23	2014-04-07	맵 파마슈티컬스, 인코포레이티드	신규한 플루오로에르골린 유사체

1979
- 1979-06-12 CH CH547679A patent/CH642082A5/de not_active IP Right Cessation
1980
- 1980-06-09 BE BE1/9842A patent/BE883711A/fr not_active IP Right Cessation
- 1980-06-11 JP JP7957580A patent/JPS562992A/ja active Granted
- 1980-06-12 ZA ZA00803516A patent/ZA803516B/xx unknown

Also Published As

Publication number	Publication date
BE883711A (fr)	1980-12-09
JPS562992A (en)	1981-01-13
ZA803516B (en)	1982-01-27
CH642082A5 (en)	1984-03-30

Publication	Publication Date	Title
KR930011300B1 (ko)	1993-11-29	옥시인돌유도체
MC1491A1 (fr)	1983-09-12	Nouveaux composes bicycliques,procedes pour les preparer et formules pharmaceutiques contenant ces composes
JPH0437836B2 (fr)	1992-06-22
US4219555A (en)	1980-08-26	2-Bromoergosine and pharmacologically compatible acid addition salts thereof as well as their use for the treatment of arterial hypertension and or heart arrythmias
EP0682947A1 (fr)	1995-11-22	Médicament pour le traitement thérapeutique prophylactique des maladies causées par une hyperplasie des cellules musculaires lisses
FI86733C (fi)	1992-10-12	Analogifoerfarande foer framstaellning av terapeutiskt anvaendbar piperazinkarboxylsyra
JPS5813542B2 (ja)	1983-03-14	シンキエルゴリンユウドウタイノセイホウ
KR102935431B1 (ko)	2026-03-05	디아미노피리미딘 화합물을 사용하여 자궁내막증-관련 통증 치료 방법
JPH0210834B2 (fr)	1990-03-09
JPS5944371A (ja)	1984-03-12	１―フエニル―２―メチル―３―（１―ピロリジニル）―１―プロパノン誘導体
US4440772A (en)	1984-04-03	Acid addition salts of dextrorotatory ergot alkaloids, a process for the preparation thereof as well as their use as medicines
KR890000813B1 (ko)	1989-04-08	에르고트 5's-(2r-부틸)펩티드 알카로이드의 제조방법
CA1110229A (fr)	1981-10-06	Obtention de derives de 3-amino-17a-aza-d- homoandrostane; produits pharmaceutiques qui en contiennent
US4547500A (en)	1985-10-15	Ergot peptide derivatives, their preparation and pharmaceutical compositions containing them
CS250683B2 (en)	1987-05-14	Method of s-(-)-3-(3-acetyl-4/3-tertiary butylamino-2-hydroxypropoxy/phenyl)-1,1-diethylurea production
CA2122290A1 (fr)	1994-10-31	Composes pyrrolopyraziniques, leurs procedes de preparation et les compositions pharmaceutiques qui les contiennent
US5096929A (en)	1992-03-17	2-amino-1,2,3,4-tetrahydronaphthalene derivatives with cardiovascular activity, process for their preparation and pharmaceutical compositions containing them
EP0207695A2 (fr)	1987-01-07	Dialkylamino-4-tétrahydrobenz[c,d]indoles
US4764517A (en)	1988-08-16	8α-(N,N-diethylsulfamoylamino)-6-n-propyl ergoline useful as a prolactin secretion inhibitor, anti-parkinson, anti-depressant agent
US20060035883A1 (en)	2006-02-16	Novel serotonin receptor ligands and their uses thereof
KR950002833B1 (ko)	1995-03-27	1, 7-치환된 헵틴-2-온 화합물의 제조 방법
US4219556A (en)	1980-08-26	Substituted-8-phenylamino ergolines
CA1147331A (fr)	1983-05-31	10-bromosandwicine, 10-bromoisosandwicine, methode de preparation, applications et composes pharmaceutiques les contenant
JPS6223753B2 (fr)	1987-05-25
US4801712A (en)	1989-01-31	2-Alkyl(or phenyl)thio-6-n-alkylergolines are dopamine D-1 antagonists without D-2 agonist activity