HU190105B - Process for production of pirazolyl-methyl-ergolin- derivatives and their acid additional salts - Google Patents
Process for production of pirazolyl-methyl-ergolin- derivatives and their acid additional salts Download PDFInfo
- Publication number
- HU190105B HU190105B HU832001A HU200183A HU190105B HU 190105 B HU190105 B HU 190105B HU 832001 A HU832001 A HU 832001A HU 200183 A HU200183 A HU 200183A HU 190105 B HU190105 B HU 190105B
- Authority
- HU
- Hungary
- Prior art keywords
- hydrogen
- formula
- alkyl
- methyl
- pyridyl
- Prior art date
Links
- 150000003839 salts Chemical class 0.000 title claims abstract description 10
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 4
- 238000000034 method Methods 0.000 title claims description 16
- 239000002253 acid Substances 0.000 title claims description 14
- 150000001875 compounds Chemical class 0.000 claims abstract description 51
- 125000004076 pyridyl group Chemical group 0.000 claims abstract description 22
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 14
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims abstract description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 10
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 9
- 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 group 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 claims abstract description 9
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims abstract description 8
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims abstract description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 46
- 239000001257 hydrogen Substances 0.000 claims description 46
- -1 methylene, carbonyl Chemical group 0.000 claims description 35
- 150000002431 hydrogen Chemical class 0.000 claims description 26
- 238000002360 preparation method Methods 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 230000000694 effects Effects 0.000 claims description 10
- 230000002829 reductive effect Effects 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 6
- 150000002923 oximes Chemical class 0.000 claims description 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 5
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- 206010029897 Obsessive thoughts Diseases 0.000 claims description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 3
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 3
- 125000005188 oxoalkyl group Chemical group 0.000 claims description 3
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- PXGPLTODNUVGFL-BRIYLRKRSA-N (E,Z)-(1R,2R,3R,5S)-7-(3,5-Dihydroxy-2-((3S)-(3-hydroxy-1-octenyl))cyclopentyl)-5-heptenoic acid Chemical compound CCCCC[C@H](O)C=C[C@H]1[C@H](O)C[C@H](O)[C@@H]1CC=CCCCC(O)=O PXGPLTODNUVGFL-BRIYLRKRSA-N 0.000 abstract 1
- 230000003389 potentiating effect Effects 0.000 abstract 1
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- 238000006243 chemical reaction Methods 0.000 description 10
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- 238000009835 boiling Methods 0.000 description 6
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- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
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- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 4
- 239000012280 lithium aluminium hydride Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
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- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 229910015900 BF3 Inorganic materials 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
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- 101800000989 Oxytocin Proteins 0.000 description 2
- 102100031951 Oxytocin-neurophysin 1 Human genes 0.000 description 2
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- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
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- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 description 1
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- DOYIYVYKJSUOOI-UHFFFAOYSA-N 2-(pyridine-3-carbonyl)cyclopentan-1-one Chemical compound C=1C=CN=CC=1C(=O)C1CCCC1=O DOYIYVYKJSUOOI-UHFFFAOYSA-N 0.000 description 1
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- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
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- 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
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- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 230000001991 pathophysiological effect Effects 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000035935 pregnancy Effects 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 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
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 229960000195 terbutaline Drugs 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 230000008359 toxicosis Effects 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
- 230000010415 tropism Effects 0.000 description 1
- 230000003191 uterotonic effect Effects 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
- C07D457/02—Heterocyclic compounds containing indolo [4, 3-f, g] quinoline ring systems, e.g. derivatives of ergoline, of the formula:, e.g. lysergic acid with hydrocarbon or substituted hydrocarbon radicals, attached in position 8
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pulmonology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Priority Applications (15)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU832001A HU190105B (en) | 1983-06-03 | 1983-06-03 | Process for production of pirazolyl-methyl-ergolin- derivatives and their acid additional salts |
| US06/615,387 US4632928A (en) | 1983-03-06 | 1984-05-30 | Pyrazole derivatives with an ergoline skeleton, their acid addition salts, and a process for the preparation thereof |
| AT84106260T ATE55129T1 (de) | 1983-06-03 | 1984-06-01 | Pyrazol-derivate mit einem ergolingeruest, verfahren zu deren herstellung und diese enthaltende pharmazeutische zusammensetzungen. |
| DE8484106260T DE3482854D1 (de) | 1983-06-03 | 1984-06-01 | Pyrazol-derivate mit einem ergolingeruest, verfahren zu deren herstellung und diese enthaltende pharmazeutische zusammensetzungen. |
| IL8471988A IL71988A (en) | 1983-06-03 | 1984-06-01 | 8beta-(1-pyrazolyl)methylergoline derivatives and acid addition salts thereof,their preparation and pharmaceutical compositions containing them |
| JP59111053A JPS6084286A (ja) | 1983-06-03 | 1984-06-01 | エルゴリン骨格を有する新規なピラゾール誘導体および医薬組成物 |
| EP84106260A EP0128479B1 (en) | 1983-06-03 | 1984-06-01 | Pyrazole derivatives with an ergoline skeleton, a process for preparing them and pharmaceutical compositions containing these compounds |
| CA000455626A CA1252086A (en) | 1983-06-03 | 1984-06-01 | Pyrazole derivatives with an ergoline skeleton, their acid addition salts, and a process for the preparation thereof |
| DK273884A DK162050C (da) | 1983-06-03 | 1984-06-01 | Pyrazolderivater med ergolinskelet eller salte deraf, deres fremstilling, farmaceutiske praeparater indeholdende disse og fremgangsmaade til fremstilling af de farmaceutiske praeparater |
| ES533086A ES8800940A1 (es) | 1983-06-03 | 1984-06-02 | Procedimiento de preparacion de nuevos derivados pirazoles con esqueleto de ergolina y de sus sales de adicion acidas |
| ZA844162A ZA844162B (en) | 1983-06-03 | 1984-06-04 | Pyrazole derivatives with an ergoline skeleton,their acid addition salts,and a process for the preparation thereof |
| FI842233A FI80272C (fi) | 1983-06-03 | 1984-06-04 | Foerfarande foer framstaellning av terapeutiskt anvaendbara pyrazolderivat med ergolinskelett samt deras syraadditionssalter. |
| AU29032/84A AU569518B2 (en) | 1983-06-03 | 1984-06-04 | Pyrazolo substituted ergolines |
| GR74906A GR82419B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1983-06-03 | 1984-06-04 | |
| AR296829A AR240323A1 (es) | 1983-06-03 | 1984-06-04 | Procedimiento para la preparacion de derivados de pirazol con esqueleto de ergolina, y procedimeitno para la preparacion de composicones farmaceruticas que los contienen. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU832001A HU190105B (en) | 1983-06-03 | 1983-06-03 | Process for production of pirazolyl-methyl-ergolin- derivatives and their acid additional salts |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| HUT34748A HUT34748A (en) | 1985-04-28 |
| HU190105B true HU190105B (en) | 1986-08-28 |
Family
ID=10957235
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU832001A HU190105B (en) | 1983-03-06 | 1983-06-03 | Process for production of pirazolyl-methyl-ergolin- derivatives and their acid additional salts |
Country Status (15)
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2173189B (en) * | 1985-02-21 | 1988-04-27 | Maruko Pharmaceutical Co | Ergoline derivatives and salts thereof and pharmaceutical compositions thereof |
| GB8702364D0 (en) * | 1987-02-03 | 1987-03-11 | Erba Farmitalia | Ergolinyl heterocycles |
| GB9603226D0 (en) * | 1996-02-15 | 1996-04-17 | Pharmacia Spa | Heterocyclyl-ergoline derivatives |
| US6369089B1 (en) | 2000-09-14 | 2002-04-09 | Allergan Sales, Inc. | Interheteroaryl 7-oxabicyclic [2.2.1]heptane oxazoles as prostaglandin F2α antagonists |
| US6407250B1 (en) | 2000-09-14 | 2002-06-18 | Allergan Sales, Inc. | Interphenylene 7-oxabicyclic [2.2.1] heptane oxazoles as prostaglandin F2a antagonists |
| US6511999B2 (en) | 2000-09-14 | 2003-01-28 | Allergan, Inc. | Interheteroaryl 7-oxabicyclic [2.2.1]heptane oxazoles as prostaglandin F2α antagonists |
| US7045634B2 (en) * | 2003-09-05 | 2006-05-16 | Allergan, Inc. | Prostamide receptor antagonists |
| CN102448965B (zh) | 2009-04-02 | 2014-06-18 | 阿勒根公司 | 前列腺素e受体拮抗剂 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1695752C3 (de) * | 1966-07-29 | 1974-06-06 | Societa Farmaceutici Italia, Mailand (Italien) | 1 ,ö-Dimethyl-ebeta-N-carbobenzoxyaminomethyl-2,3-dihydro-1 Oalpha-ergolin und ein Verfahren zu seiner Herstellung |
| US4134987A (en) * | 1976-01-14 | 1979-01-16 | Huppatz John L | Compounds and compositions |
| HU178396B (en) * | 1978-03-20 | 1982-04-28 | Vianova Kunstharz Ag | Process for producing new 8-beta-hydrazion-methyl-ergoline-and -ergolene derivatives |
| GB2056437A (en) * | 1979-08-07 | 1981-03-18 | Erba Farmitalia | Secoergoline derivatives |
| GB2120242A (en) * | 1982-04-30 | 1983-11-30 | Erba Farmitalia | Ergoline derivatives |
-
1983
- 1983-06-03 HU HU832001A patent/HU190105B/hu not_active IP Right Cessation
-
1984
- 1984-05-30 US US06/615,387 patent/US4632928A/en not_active Expired - Fee Related
- 1984-06-01 AT AT84106260T patent/ATE55129T1/de not_active IP Right Cessation
- 1984-06-01 IL IL8471988A patent/IL71988A/xx unknown
- 1984-06-01 DK DK273884A patent/DK162050C/da not_active IP Right Cessation
- 1984-06-01 CA CA000455626A patent/CA1252086A/en not_active Expired
- 1984-06-01 EP EP84106260A patent/EP0128479B1/en not_active Expired - Lifetime
- 1984-06-01 JP JP59111053A patent/JPS6084286A/ja active Granted
- 1984-06-01 DE DE8484106260T patent/DE3482854D1/de not_active Expired - Lifetime
- 1984-06-02 ES ES533086A patent/ES8800940A1/es not_active Expired
- 1984-06-04 GR GR74906A patent/GR82419B/el unknown
- 1984-06-04 AR AR296829A patent/AR240323A1/es active
- 1984-06-04 FI FI842233A patent/FI80272C/fi not_active IP Right Cessation
- 1984-06-04 AU AU29032/84A patent/AU569518B2/en not_active Ceased
- 1984-06-04 ZA ZA844162A patent/ZA844162B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU569518B2 (en) | 1988-02-04 |
| EP0128479A2 (en) | 1984-12-19 |
| FI80272C (fi) | 1990-05-10 |
| EP0128479B1 (en) | 1990-08-01 |
| FI80272B (fi) | 1990-01-31 |
| GR82419B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1984-12-13 |
| DE3482854D1 (de) | 1990-09-06 |
| DK273884D0 (da) | 1984-06-01 |
| IL71988A0 (en) | 1984-10-31 |
| JPH0342274B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1991-06-26 |
| DK162050B (da) | 1991-09-09 |
| US4632928A (en) | 1986-12-30 |
| AR240323A1 (es) | 1990-03-30 |
| HUT34748A (en) | 1985-04-28 |
| ZA844162B (en) | 1984-12-24 |
| AU2903284A (en) | 1984-12-06 |
| IL71988A (en) | 1987-01-30 |
| ES8800940A1 (es) | 1987-12-01 |
| ES533086A0 (es) | 1987-12-01 |
| EP0128479A3 (en) | 1985-10-30 |
| DK162050C (da) | 1992-02-10 |
| FI842233A7 (fi) | 1984-12-04 |
| FI842233A0 (fi) | 1984-06-04 |
| JPS6084286A (ja) | 1985-05-13 |
| ATE55129T1 (de) | 1990-08-15 |
| DK273884A (da) | 1984-12-04 |
| CA1252086A (en) | 1989-04-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HU90 | Patent valid on 900628 | ||
| HMM4 | Cancellation of final prot. due to non-payment of fee |