NO169188B - Kombinert sluseroerventil og stengeventil - Google Patents
Kombinert sluseroerventil og stengeventil Download PDFInfo
- Publication number
- NO169188B NO169188B NO831924A NO831924A NO169188B NO 169188 B NO169188 B NO 169188B NO 831924 A NO831924 A NO 831924A NO 831924 A NO831924 A NO 831924A NO 169188 B NO169188 B NO 169188B
- Authority
- NO
- Norway
- Prior art keywords
- acid
- dimethyl
- ergoline
- carbon atoms
- dihydro
- Prior art date
Links
- 238000000034 method Methods 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 125000002252 acyl group Chemical group 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 6
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- TWBYWOBDOCUKOW-UHFFFAOYSA-N isonicotinic acid Chemical compound OC(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-N 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical class OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- -1 nitro, hydroxyl Chemical group 0.000 claims description 4
- UNELDXFWWQRODL-IUODEOHRSA-N (6ar,10ar)-4,7-dimethyl-6,6a,8,9,10,10a-hexahydroindolo[4,3-fg]quinoline Chemical class C1=CC([C@H]2CCCN([C@@H]2C2)C)=C3C2=CN(C)C3=C1 UNELDXFWWQRODL-IUODEOHRSA-N 0.000 claims description 3
- 150000007513 acids Chemical class 0.000 claims description 3
- 229940098779 methanesulfonic acid Drugs 0.000 claims description 3
- 239000011664 nicotinic acid Substances 0.000 claims description 3
- 229960003512 nicotinic acid Drugs 0.000 claims description 3
- 235000001968 nicotinic acid Nutrition 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
- 230000010933 acylation Effects 0.000 claims description 2
- 238000005917 acylation reaction Methods 0.000 claims description 2
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 claims description 2
- 150000008064 anhydrides Chemical class 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 150000001735 carboxylic acids Chemical class 0.000 claims 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 26
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 13
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 238000010521 absorption reaction Methods 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 230000008018 melting Effects 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- 229940076279 serotonin Drugs 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 4
- CBYOKKIRJYELKD-AVPYDZBYSA-N [(6aR,9S,10aR)-4,7-dimethyl-5,5a,6,6a,8,9,10,10a-octahydroindolo[4,3-fg]quinolin-9-yl]methanamine Chemical compound CN1CC2C[C@H]3N(C[C@@H](C[C@@H]3C=3C=CC=C1C=32)CN)C CBYOKKIRJYELKD-AVPYDZBYSA-N 0.000 description 4
- 230000000794 anti-serotonin Effects 0.000 description 4
- 239000003420 antiserotonin agent Substances 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
- 235000011121 sodium hydroxide Nutrition 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- MBIZFBDREVRUHY-UHFFFAOYSA-N 2,6-Dimethoxybenzoic acid Chemical compound COC1=CC=CC(OC)=C1C(O)=O MBIZFBDREVRUHY-UHFFFAOYSA-N 0.000 description 2
- LULAYUGMBFYYEX-UHFFFAOYSA-N 3-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 206010020751 Hypersensitivity Diseases 0.000 description 2
- 208000001953 Hypotension Diseases 0.000 description 2
- ILUJQPXNXACGAN-UHFFFAOYSA-N O-methylsalicylic acid Chemical compound COC1=CC=CC=C1C(O)=O ILUJQPXNXACGAN-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
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 230000002908 adrenolytic effect Effects 0.000 description 2
- 208000026935 allergic disease Diseases 0.000 description 2
- 230000007815 allergy Effects 0.000 description 2
- 239000013068 control sample Substances 0.000 description 2
- JBDSSBMEKXHSJF-UHFFFAOYSA-N cyclopentanecarboxylic acid Chemical compound OC(=O)C1CCCC1 JBDSSBMEKXHSJF-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 208000021822 hypotensive Diseases 0.000 description 2
- 230000001077 hypotensive effect Effects 0.000 description 2
- ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluic acid Chemical compound CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 description 2
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 2
- LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical compound OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 description 2
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 2
- 229910003446 platinum oxide Inorganic materials 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
- GYSCBCSGKXNZRH-UHFFFAOYSA-N 1-benzothiophene-2-carboxamide Chemical compound C1=CC=C2SC(C(=O)N)=CC2=C1 GYSCBCSGKXNZRH-UHFFFAOYSA-N 0.000 description 1
- HZNQSWJZTWOTKM-UHFFFAOYSA-N 2,3,4-trimethoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C(OC)=C1OC HZNQSWJZTWOTKM-UHFFFAOYSA-N 0.000 description 1
- QRAFJHXNLQTXQW-UHFFFAOYSA-N 2-methylpropyl hydrogen carbonate Chemical compound CC(C)COC(O)=O QRAFJHXNLQTXQW-UHFFFAOYSA-N 0.000 description 1
- SLAMLWHELXOEJZ-UHFFFAOYSA-N 2-nitrobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1[N+]([O-])=O SLAMLWHELXOEJZ-UHFFFAOYSA-N 0.000 description 1
- ZRPLANDPDWYOMZ-UHFFFAOYSA-N 3-cyclopentylpropionic acid Chemical compound OC(=O)CCC1CCCC1 ZRPLANDPDWYOMZ-UHFFFAOYSA-N 0.000 description 1
- XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 1
- AWQSAIIDOMEEOD-UHFFFAOYSA-N 5,5-Dimethyl-4-(3-oxobutyl)dihydro-2(3H)-furanone Chemical compound CC(=O)CCC1CC(=O)OC1(C)C AWQSAIIDOMEEOD-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- GHVNFZFCNZKVNT-UHFFFAOYSA-N Decanoic acid Natural products CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 1
- APRJFNLVTJWEPP-UHFFFAOYSA-N Diethylcarbamic acid Chemical compound CCN(CC)C(O)=O APRJFNLVTJWEPP-UHFFFAOYSA-N 0.000 description 1
- 206010019233 Headaches Diseases 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 208000019695 Migraine disease Diseases 0.000 description 1
- SGXDXUYKISDCAZ-UHFFFAOYSA-N N,N-diethylglycine Chemical compound CCN(CC)CC(O)=O SGXDXUYKISDCAZ-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- YKIOKAURTKXMSB-UHFFFAOYSA-N adams's catalyst Chemical compound O=[Pt]=O YKIOKAURTKXMSB-UHFFFAOYSA-N 0.000 description 1
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 230000001387 anti-histamine Effects 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 239000000739 antihistaminic agent Substances 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 1
- NJAPCAIWQRPQPY-UHFFFAOYSA-N benzyl hydrogen carbonate Chemical compound OC(=O)OCC1=CC=CC=C1 NJAPCAIWQRPQPY-UHFFFAOYSA-N 0.000 description 1
- GONOPSZTUGRENK-UHFFFAOYSA-N benzyl(trichloro)silane Chemical compound Cl[Si](Cl)(Cl)CC1=CC=CC=C1 GONOPSZTUGRENK-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- DFFDSQBEGQFJJU-UHFFFAOYSA-N butyl hydrogen carbonate Chemical compound CCCCOC(O)=O DFFDSQBEGQFJJU-UHFFFAOYSA-N 0.000 description 1
- 230000001914 calming effect Effects 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- 229940106681 chloroacetic acid Drugs 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 1
- HWJHWSBFPPPIPD-UHFFFAOYSA-N ethoxyethane;propan-2-one Chemical compound CC(C)=O.CCOCC HWJHWSBFPPPIPD-UHFFFAOYSA-N 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 231100000869 headache Toxicity 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- LPAGFVYQRIESJQ-UHFFFAOYSA-N indoline Chemical class C1=CC=C2NCCC2=C1 LPAGFVYQRIESJQ-UHFFFAOYSA-N 0.000 description 1
- 208000027866 inflammatory disease Diseases 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- ZAGRKAFMISFKIO-QMTHXVAHSA-N lysergic acid Chemical class C1=CC(C2=C[C@H](CN([C@@H]2C2)C)C(O)=O)=C3C2=CNC3=C1 ZAGRKAFMISFKIO-QMTHXVAHSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 206010027599 migraine Diseases 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- CQDGTJPVBWZJAZ-UHFFFAOYSA-N monoethyl carbonate Chemical compound CCOC(O)=O CQDGTJPVBWZJAZ-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000021962 pH elevation Effects 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- AHIHJODVQGBOND-UHFFFAOYSA-N propan-2-yl hydrogen carbonate Chemical compound CC(C)OC(O)=O AHIHJODVQGBOND-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- FOWDZVNRQHPXDO-UHFFFAOYSA-N propyl hydrogen carbonate Chemical compound CCCOC(O)=O FOWDZVNRQHPXDO-UHFFFAOYSA-N 0.000 description 1
- ATBIAJXSKNPHEI-UHFFFAOYSA-N pyridine-3-carbonyl chloride Chemical compound ClC(=O)C1=CC=CN=C1 ATBIAJXSKNPHEI-UHFFFAOYSA-N 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 206010044652 trigeminal neuralgia Diseases 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- 210000004291 uterus Anatomy 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
- 229940124549 vasodilator Drugs 0.000 description 1
- 239000003071 vasodilator agent Substances 0.000 description 1
Classifications
-
- E—FIXED CONSTRUCTIONS
- E21—EARTH OR ROCK DRILLING; MINING
- E21B—EARTH OR ROCK DRILLING; OBTAINING OIL, GAS, WATER, SOLUBLE OR MELTABLE MATERIALS OR A SLURRY OF MINERALS FROM WELLS
- E21B34/00—Valve arrangements for boreholes or wells
- E21B34/02—Valve arrangements for boreholes or wells in well heads
- E21B34/04—Valve arrangements for boreholes or wells in well heads in underwater well heads
- E21B34/045—Valve arrangements for boreholes or wells in well heads in underwater well heads adapted to be lowered on a tubular string into position within a blow-out preventer stack, e.g. so-called test trees
-
- E—FIXED CONSTRUCTIONS
- E21—EARTH OR ROCK DRILLING; MINING
- E21B—EARTH OR ROCK DRILLING; OBTAINING OIL, GAS, WATER, SOLUBLE OR MELTABLE MATERIALS OR A SLURRY OF MINERALS FROM WELLS
- E21B2200/00—Special features related to earth drilling for obtaining oil, gas or water
- E21B2200/04—Ball valves
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Geology (AREA)
- Mining & Mineral Resources (AREA)
- Physics & Mathematics (AREA)
- Environmental & Geological Engineering (AREA)
- Fluid Mechanics (AREA)
- General Life Sciences & Earth Sciences (AREA)
- Geochemistry & Mineralogy (AREA)
- Safety Valves (AREA)
- Catching Or Destruction (AREA)
- Mechanically-Actuated Valves (AREA)
Description
Fremgangsmåte ved fremstilling av terapeutisk
aktive derivater av 1,6-dimethyl-10a-ergolin.
Foreliggende oppfinnelse angår en fremgangsmåte ved fremstilling av nye terapeutisk aktive derivater åv 1,6-dimethyl-lOa-ergoiin
med formelen:
hvor R er en acylgruppe av en eventuelt med. halogen-, fenyl-, fenoxy-, alkoxy- eller dialkylaminogrupper, hvor alkylgruppen har 1- k carbonatomer, substituert alifatisk carboxylsyre med 1-10 carbonatomer, en acylgruppe av en cycloalifatisk carboxylsyre med 5 carbonatomer i den cycloalifatiske ring, en acylgruppe av en eventuelt med halogen-, nitro-, hydroxyl-, alkyl eller alkoxygrupper, hvor alkylgruppen har 1- h carbonatomer, substituert aromatisk carboxylsyre med ikke over 10 carbonatomer, acylgruppen av nicotinsyre eller isonicotinsyre, eller resten av methansulfonsyre eller toluensulfonsyre.
8p-N-acylaminomethylderivater av l,6-dimethyl-10a-ergolin med anti-serotonin, veefrembringende, adrenolytisk, hypotensiv og beroligende virkning er beskrevet, se britisk patent nr. 959 261.
Det har nu overraskende vist seg at de ifolge fremgangsmåten fremstilte produkter ikke bare besitter en god veefrembringende adrenolytisk, hypotensiv og beroligende virkning, men også en for-holdsvis hoy antiserotonin virkning sammen med en meget gunstig assimilasjon sammenlignet med de tilsvarende produkter hvis carbonatomer i 2,3-posisjon er forbundet med en dobbeltbinding.
De ifolge foreliggende fremgangsmåte fremstilte produkter besitter derfor en betydelig terapeutisk fordel sammenlignet med de kjente forbindelser da de har en hurtigere virkning og kan anvendes i mindre doser.
Produktene fremstilt ifolge foreliggende fremgangsmåte fremstilles ved en metode basert på reduksjon av l,6-dimethyl-8p-aminomethyl-10a-ergolin,. som er beskrevet i britisk patent nr. 959 261, med påfolgende acylering av det erholdte l,6-dimethyl-8p-aminomethyl-2,3-dihydro-lOa-ergolin.
Reduksjonen av 1,6-dimethyl-8p-aminomethyl-10a-ergolin utfores fortrinnsvis ved den fremgangsmåte som er beskrevet av A. Smith og ;medarbeidere i Chem. Comm. 1965, nr. 18, side h27. Denne fremgangsmåte som ved foreliggende fremgangsmåte for forste gang- med suksess er blitt anvendt for ergolinderivater, består i det vesentlige i at utgangsforbindelsen opploses i et polart opplosningsmiddel, f.eks. iethanol, vann eller blandinger av disse, og i en opplosning av jfluorsyre eller andre sterke syrer, hvorpå den fremstilte opplosning jhydrogeneres ved værelsetemperatur og atmosfæretrykk i nærvær av en katalysator, f.eks. platinaoxyd.. _
Det fremstilte 1,6-dimethyl-8p-aminomethyl-2,3-dihydro-10a-ergolin rystes etter alkalinisering ut av reaksjonsblandingen ved hjelp av et egnet organisk opplosningsmiddel.
De tilsvarende N-acylderivater fremstilles ved reaksjon av 1,6-dimethyl-8p-aminomethyl-2,3-dihydro-10a-ergolinet med .et acyl-eringsmiddel, f.eks. anhydridet eller kloridet av en egnet syre, eventuelt i nærvær av et tertiært amin, f.eks. pyridin, diethylamin og triethylamin. Derivater av de folgende syrer representerer typiske eksempler på de ved foreliggende fremgangsmåte fremstilte acylderivater; eddiksyre, trimethyleddiksyre, propionsyre, smor-
syre, valeriansyre, hexansyre, heptansyre, octansyre, dekansyre, cyclopentancarboxylsyre, cyclopentylpropionsyre, ravsyre, benzoe-syre, 2-nitrobenzoesyre, 3-klorbenzoesyre, salicylsyre, methyl-benzoesyre, 2-methoxybenzoesyre, 2,6-dimethoxybenzoesyre , 3 A j5""tri-methoxybenzoesyre, fenylpropionsyre, fenoxyeddiksyre, a-fenoxy-propionsyre, diethylcarbaminsyre, kloreddiksyre, N,N-diethylamino-eddiksyre, trimethyleddiksyre, a-fenoxysmorsyre, butylkullsyre, isobutylkullsyre, ethylkullsyre, propylkullsyre, isopropylkullsyre, benzylkullsyre, p-toluensulfonsyre, methansulfonsyre, nicotinsyre og isonicotinsyre.
Farmakologi.
De ved foreliggende fremgangsmåte fremstilte forbindelser kan anvendes som analgetiske, antihistaminske og antiflogistiske midler og kan administreres oralt, rektalt og parenteralt. De viser folgende kliniske indikasjoner: migrene, hodepine, trigeminusneuralgi, generell allergi og inflammasjonssykdommer.
l,6-dimethyl-8p-N-carbobenzoxyaminomethyl-2,3-dihydro-10a-ergolin., 1,6-dimethyl-8p-propionamidomethyl-2,3-dihydro-10a-ergolin og l,6-dimethyl-8p-nicotinamidomethyl-2,3-dihydro-10a-ergolin er noen av de ved foreliggende fremgangsmåte fremstilte forbindelser som er istand til å motvirke den på grunn av serotonin utloste virkning. Disse forbindelsers virksomhet ble fastslått ved sammenligning med virkningen til hhv. 1-methyl-N-carbobenzoxydihydrolysergamin, 1-methyl-N-propionyldihydro-D-lysergamin og 1-methyl-N-nicotinyldihydro-D-
Den anti-serotonine virkning ble bestemt "in vitro" ved den fremgangsmåte som er beskrevet av Stone og medarbeidere i J. Pharm. Exp. Ther. 131. 1961,- side--73} og som beror på hemningen av den-serotonin-
betingede kontraksjon av rotteuterus.
I dennsteiTtstående tabell 1 er de oppnådde resultater angitt som ECcq (effektiv konsentrasjon 50), dvs. den konsentrasjon (ly/cm3) som er istand til å frembringe en 50 % hemning av serotoninvirkningen ved en serotoninkonsentrasjon av OjOly/cm^.
Anti-serotoninvirkningen "in vivo" ble bestemt ved hjelp av fremgangsmåten beskrevet av W. Doepfner og A. Cerletti (Int. Arch.
i Allergy 12,side 89. - 97, 1958) og som beror på en 50 % hemning av >' den av serotonin forårsakede vannansamling i rottepoter.
I tabell 2 er de oppnådde resultater angitt som ED^q, dvs. den dose (i mg/kg) som frembringer en 50 % hemning av sérotonin-yirkhingen f or de med den undersakte forbihdélse i avtrappede doser, behandlede dyr under hensyntagen tilde forskjellige tidsrom mellom administreringen av den angjeldende forbindelse og serotoninet.
Toksisiteten til l,6-dimethyl-8p-N-carbobenzoxyaminomethyl-2,3-dihydro-lOa-ergolin ble bestemt i overensstemmelse med de for-sbk som i alminnelighet benyttes i forbindelse med lysergsyrederi-yater.
EKSEMPEL 1
Fremstilling av mellomproduktet
■ 1. 6- dlmethyl- 8p- aminomethyl- 2. 3- dihydro- 10a- ergolin 110 mg platinaoxyd (Adams katalysator) ble satt til en opplosning av 2 g l,6-dimethyl-8p-aminomethyl-10a-ergolin i 15 ml
ethanol og 20 ml 31 % fluorsyre, og blandingen ble hydrogenert
ved værelsetemperatur og atmosfæretrykk. Reduksjonsforlopet ble fulgt ved å overvåke den erholdte opplosnings U.V.-absorpsjon, hvor-ved en kontrollprove ble tatt og fortynnet med ethanol. Hydrogen-eringen ble anéett som avsluttet da kontrollproven oppviste den typiske U.V.-absorpsjonskurve for 2,3-dihydroindol-derivatet. Derpå ble reaksjonsblandingen gjort alkalisk med natriumcarbonat, og det fremstilte 1,6-dimethyl-8p-aminomethyl-2,3-dihydro-10a-ergolin ble ekstrahert med methylenklorid. Ved rekrystallisering av den etter inndampning gjenværende rest fra methanolether ble 600 mg produkt oppnådd, som smelter ved 13<*>+ - 136°C.
<Absorpsjonsmaksima i U.V. ved 252 og 292 mu.)
EKSEMPEL 2
l, 6- dimethyl- 8B- N- carbobenzoxyaminomethyl- 2, 3- dihydro- 10a- ergolin
600 mg 1,6-dimethyl-8p-aminomethyl-2,3-dihydro-10a-ergolin
ble oppslemmet i en blanding av 0,6 ml pyridin og 3 ml kloroform, hvorpå en opplosning av 0,65 ml klormaursyrebenzylester i 5 ml kloroform med en temperatur mellom -10 og 0°C ble dråpevis tilsatt. Blandingen fikk henstå i 1 time ved værelsetemperatur og ble derpå utrystet med vandig natriumbicarbonatopplosning og med vann. Det organiske lag ble så inndampet, den erholdte rest blandet med ethyl-ether og 1,6-dimethyl~8p-carbobenzoxyaminomethyl-2,3-dihydro-10a-ergolinet isolert. Ved rekrystallisering fra aceton-ether ble 500 mg produkt oppnådd som smeltet ved 161 - 163°C.
(Absorpsjonsmaksima i U.V. ved 252 og 292 np)
EKSEMPEL 3
l, 6- dimethyl- 8B- acetamidomethyl- 2. 3- dihydro- lQq- ergolin
0,25 ml acetylklorid ble ved en temperatur av 15°C dråpevis satt til en opplosning av 500 mg 1,6-dimethyl-8B-aminomethyl-2,3-dihydro-lOcc-ergolin i 11 ml pyridin. Blandingen fikk henstå i 30 minutter ved denne temperatur og så i 1 time ved værelsetemperatur under omroring, hvorpå det til å begynne med dannede bunnfall forsvant. Reaksjonsblandingen ble heldt over i en blanding av 60 ml klOTOform, 10 ml methanol oglOml lN.hatronlut. Det organiske lag ble grundig Vasket med vann, inndampet og den erholdte rest rekrystallisert fra aceton. Det ble oppnådd 300 mg av et produkt som smeltet ved 223 - 226°C. [a]D = -79,2° (c = 0,25 i pyridin), (U.V.-absorps jonsmaksima ved 252 og 293 nyu.).
EKSEMPEL k 1. 6- dimethyl- 8B- cyclopentylpropionamidomethyl- 2 ? 3- dihydro- lOa- ergolin 550 mg B-cyclopentylpropionylklorid ble ved 0°C dråpevis satt til 500 mg l,6-dimethyl-8p-aminomethyl-2,3-dihydro-10a-ergolin i 11 ml pyridin. Opplosningen ble under omroring holdt ved 0°C i 30 minutter og ved værelsetemperatur i 1 time. Opplosningen ble så heldt over i en blanding av 65 ml kloroform, 10 ml methanol og 10 ml 1N-natronlut. Det med vann vaskede organiske lag ble inndampet, og den erholdte rest rekrystallisert fra aceton. Det ble oppnådd *+00 mg av et produkt som smeltet ved 203 - 205°C. [a]D = -60,3°C (c= 0,22 i pyridin): (Absorpsjonsmaksima i U.V. ved 252 og 293 np).
EKSEMPEL 5
1. 6- dimethyl- 8B- benzamidomethyl- 2. 3- dihydro- 10a- ergolin
500 mg l,6-dimethyl-8p-aminomethyl-2,3-dihydro-10a-ergolin ble opplost i 11 ml pyridin, og 0,35 ml benzoylklorid ble dråpevis tilsatt ved en temperatur mellom -15 og-10°C. Opplosningen ble så holdt ved denne temperatur i 30 minutter under omroring og derpå ved værelsetemperatur i 1 time, hvoretter opplosningen ble heldt over i en blanding av 60 ml kloroform, 10 ml methanol og 10 ml 1N-natronlut. Det organiske lag ble adskilt, vasket med vann og inndampet. Den erholdte rest ble rekrystallisert fra aceton, og det ble oppnådd 350 mg av et produkt som smeltet- ved 239 - 2^-l°C.
[a]D= -75,2° (c = 0,25 i pyridin): (Absorpsjonsmaksima i U.V. ved 29»+ mpi).
EKSEMPEL 6
1. 6- dimethyl- 8B- nic. otinamidomethyl- 2. 3- dihydro- 10a- ergolin
800 mg nicotinylklorid ble i små andeler ved værelsetemperatur og under omroring i lopet av 30 minutter satt til 500 mg 1,6-dimethyl-8p-aminomethyl-2,3-dihydro-10a-ergolin i 20 ml pyridin,
Et bunnfall ble til å begynne med dannet, men bunnfallet forsvant ptlBf^aET"ca.halvparten av reaksjonsmidlet var blitt tilsatt. Opplosningen fikk henstå i 1 time ved værelsetemperatur og ble så satt til en blanding av ikO ml kloroform, 20 ml methanol og 30 ml 1N-natronlut.
Det vannvaskede organiske lag ble inndampet, og den erholdte rest ble rekrystallisert fra aceton.
Det ble oppnådd 300 mg av et produkt som smeltet ved 230-
232°C. [a]D = 60°C (c = 0,21 1 pyridin): (Absorpsjonsmaksima i U.V. ved 253 og 29<*>+ imi).
Andre produkter med den ovenfor angitte formel ble fremstilt
ved hjelp av den samme fremgangsmåte.
Blant disse produkter var de viktigste: 1,6-dimethyl-8B-carbethoxyaminomethyl-2,3-dihydro-10a-ergolin, smeltepunkt 165°C, [a]^° = -61° (c = 0,25 pyridin),
1,6-dimethyl-80-propionamidomethyl-2,3-dihydro-10a-ergolin, smeltepunkt 209 - 211°C, [o]^<0> = -66° (c = 0,22 pyridin) og 1,6-dimethyl-8p-fenylacetamidomethyl-2,3-dihydro-10a-ergolin, smeltepunkt 225°C, [<x]p° = -58° (c = 0,21 pyridin).
Claims (1)
- " j Fremgangsmåte ved fremstilling av nye, terapeutisk aktive derivater av l,6-dimethyl-10a-ergolin med formelenhvor R er en acylgruppe av en eventuelt med halogen-, fenyl-, fenoxy-, alkoxy- eller dialkylaminogrupper, hvor alkylgruppen har 1- h carbonatomer, substituert alifatisk carboxylsyre med 1-10 carbonatomer, en acylgruppe av en cycloalifatisk carboxylsyre med 5 carbonatomer i den cycloalifatiske ring, en acylgruppe av en eventuelt med halogen-, nitro-, hydroxyl-, alkyl- eller alkoxygrupper, hvor alkylgruppen har 1-*+ carbonatomer, substituert aromatisk carboxylsyre med ikke over 10 carbonatomer, acylgruppcn av nicotinsyre eller isonicotinsyre, eller resten av methansulfonsyre eller toluensulfonsyre, karakterisert ved at 1,6-dimethyl-80-aminomethyl-lOa-crgolin hydrogeneres i fluorborsyrc eller i en annen sterk syre og ethanol i nærvær av en katalysator, og at det således erholdte 1,6-dimethyl-80-aminomethyl-2,3-dihydro-10a-ergolin over-fores til acylderivatet ved acylering med kloridet eller anhydridet til en av de ovennevnte syrer.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US06/437,172 US4522370A (en) | 1982-10-27 | 1982-10-27 | Valve |
Publications (3)
Publication Number | Publication Date |
---|---|
NO831924L NO831924L (no) | 1984-04-30 |
NO169188B true NO169188B (no) | 1992-02-10 |
NO169188C NO169188C (no) | 1992-05-20 |
Family
ID=23735378
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO831924A NO169188C (no) | 1982-10-27 | 1983-05-30 | Kombinert sluseroerventil og stengeventil |
Country Status (5)
Country | Link |
---|---|
US (1) | US4522370A (no) |
CA (1) | CA1200758A (no) |
GB (1) | GB2129033B (no) |
NO (1) | NO169188C (no) |
SG (1) | SG63688G (no) |
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FR2557664B1 (fr) * | 1983-12-28 | 1986-08-29 | Flopetrol | Vanne de securite, en particulier pour fermer un puits de petrole |
US4621695A (en) * | 1984-08-27 | 1986-11-11 | Camco, Incorporated | Balance line hydraulically operated well safety valve |
US4693315A (en) * | 1985-08-12 | 1987-09-15 | Otis Engineering Corporation | Bleedoff tool for well test system |
US4640363A (en) * | 1985-08-12 | 1987-02-03 | Otis Engineering Corporation | Bleedoff tool for well test system |
US4901798A (en) * | 1986-05-27 | 1990-02-20 | Mahmood Amani | Apparatus and method for removal of accumulated liquids in hydrocarbon producing wells |
US4880060A (en) * | 1988-08-31 | 1989-11-14 | Halliburton Company | Valve control system |
US5918670A (en) * | 1991-08-31 | 1999-07-06 | Expro North Sea Limited | Multi-sensor relief valve well test system |
US5284209A (en) * | 1992-08-19 | 1994-02-08 | Halliburton Company | Coiled tubing cutting modification |
US5431846A (en) * | 1993-05-20 | 1995-07-11 | Lever Brothers Company, Division Of Conopco, Inc. | Copolymers and detergent compositions containing them |
US5551665A (en) * | 1994-04-29 | 1996-09-03 | Halliburton Company | Ball valve with coiled tubing cutting ability |
US5806598A (en) * | 1996-08-06 | 1998-09-15 | Amani; Mohammad | Apparatus and method for removing fluids from underground wells |
US5803175A (en) * | 1996-04-17 | 1998-09-08 | Myers, Jr.; William Desmond | Perforating gun connection and method of connecting for live well deployment |
US5682921A (en) * | 1996-05-28 | 1997-11-04 | Baker Hughes Incorporated | Undulating transverse interface for curved flapper seal |
GB2313610B (en) * | 1996-05-29 | 2000-04-26 | Baker Hughes Inc | Method of performing a downhole operation |
US5782304A (en) * | 1996-11-26 | 1998-07-21 | Garcia-Soule; Virgilio | Normally closed retainer valve with fail-safe pump through capability |
AU6672198A (en) | 1997-02-21 | 1998-09-22 | Pes, Inc. | Integrated power and control system |
GB2326892B (en) * | 1997-07-02 | 2001-08-01 | Baker Hughes Inc | Downhole lubricator for installation of extended assemblies |
US6179052B1 (en) | 1998-08-13 | 2001-01-30 | Halliburton Energy Services, Inc. | Digital-hydraulic well control system |
US6567013B1 (en) | 1998-08-13 | 2003-05-20 | Halliburton Energy Services, Inc. | Digital hydraulic well control system |
US6206338B1 (en) * | 1999-12-22 | 2001-03-27 | Abb Vetco Gray, Inc. | Fail as-is hydraulic actuator |
US7389818B2 (en) * | 2002-08-21 | 2008-06-24 | Hoeiland Oddgeir | Method and device by a displacement tool |
US7776441B2 (en) * | 2004-12-17 | 2010-08-17 | Sabic Innovative Plastics Ip B.V. | Flexible poly(arylene ether) composition and articles thereof |
US7624792B2 (en) * | 2005-10-19 | 2009-12-01 | Halliburton Energy Services, Inc. | Shear activated safety valve system |
US7584797B2 (en) * | 2006-04-04 | 2009-09-08 | Stinger Wellhead Protection, Inc. | Method of subsurface lubrication to facilitate well completion, re-completion and workover |
US8887814B2 (en) * | 2006-11-07 | 2014-11-18 | Halliburton Energy Services, Inc. | Offshore universal riser system |
US7810571B2 (en) * | 2006-11-09 | 2010-10-12 | Baker Hughes Incorporated | Downhole lubricator valve |
US8225871B2 (en) * | 2006-11-09 | 2012-07-24 | Baker Hughes Incorporated | Bidirectional sealing mechanically shifted ball valve for downhole use |
US8113286B2 (en) * | 2006-11-09 | 2012-02-14 | Baker Hughes Incorporated | Downhole barrier valve |
US7905292B2 (en) * | 2009-02-06 | 2011-03-15 | Baker Hughes Incorporated | Pressure equalization device for downhole tools |
GB2485660B (en) * | 2009-05-04 | 2012-08-08 | Schlumberger Holdings | Subsea control system |
US8393396B2 (en) * | 2009-07-11 | 2013-03-12 | Baker Hughes Incorporated | Subterranean valve operated by string relative movement |
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US9163480B2 (en) | 2012-02-10 | 2015-10-20 | Halliburton Energy Services, Inc. | Decoupling a remote actuator of a well tool |
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WO2016010589A1 (en) * | 2014-07-17 | 2016-01-21 | Schlumberger Canada Limited | Simplified isolation valve for esp/well control application |
RU2704161C1 (ru) * | 2018-11-29 | 2019-10-24 | Общество с ограниченной ответственностью "Газпром 335" | Верхний изолирующий клапан |
US11655902B2 (en) * | 2019-06-24 | 2023-05-23 | Onesubsea Ip Uk Limited | Failsafe close valve assembly |
US11796070B2 (en) * | 2019-06-24 | 2023-10-24 | Onesubsea Ip Uk Limited | Ball valve assembly |
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Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US1679370A (en) * | 1927-04-30 | 1928-08-07 | Merco Nordstrom Valve Co | Valve |
US3568715A (en) * | 1968-02-08 | 1971-03-09 | Otis Eng Co | Well tools |
US3821962A (en) * | 1972-01-03 | 1974-07-02 | Hydril Co | Well tool |
US3830297A (en) * | 1973-01-08 | 1974-08-20 | Baker Oil Tools Inc | Sub-surface safety valve with improved balancing valve means |
US3842913A (en) * | 1973-05-14 | 1974-10-22 | Hydril Co | Method and apparatus for a subsurface safety valve operating with differential annular pressure |
US3941141A (en) * | 1974-05-03 | 1976-03-02 | Robert Eddie L | Blowout preventer locking apparatus and method |
US4062406A (en) * | 1976-10-15 | 1977-12-13 | Baker International Corporation | Valve and lubricator apparatus |
US4149698A (en) * | 1977-04-13 | 1979-04-17 | Otis Engineering Corporation | Surface controlled subsurface safety valve |
US4368871A (en) * | 1977-10-03 | 1983-01-18 | Schlumberger Technology Corporation | Lubricator valve apparatus |
-
1982
- 1982-10-27 US US06/437,172 patent/US4522370A/en not_active Expired - Lifetime
-
1983
- 1983-04-21 CA CA000426464A patent/CA1200758A/en not_active Expired
- 1983-04-25 GB GB08311204A patent/GB2129033B/en not_active Expired
- 1983-05-30 NO NO831924A patent/NO169188C/no unknown
-
1988
- 1988-09-28 SG SG63688A patent/SG63688G/en unknown
Also Published As
Publication number | Publication date |
---|---|
SG63688G (en) | 1989-03-10 |
NO831924L (no) | 1984-04-30 |
GB2129033B (en) | 1986-03-19 |
US4522370A (en) | 1985-06-11 |
NO169188C (no) | 1992-05-20 |
CA1200758A (en) | 1986-02-18 |
GB8311204D0 (en) | 1983-06-02 |
GB2129033A (en) | 1984-05-10 |
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