DE2459630C3 - 2-Pyrimidyl-aminomethylergolinderivate, Verfahren zu ihrer Herstellung und pharmazeutische Mittel - Google Patents
2-Pyrimidyl-aminomethylergolinderivate, Verfahren zu ihrer Herstellung und pharmazeutische MittelInfo
- Publication number
- DE2459630C3 DE2459630C3 DE2459630A DE2459630A DE2459630C3 DE 2459630 C3 DE2459630 C3 DE 2459630C3 DE 2459630 A DE2459630 A DE 2459630A DE 2459630 A DE2459630 A DE 2459630A DE 2459630 C3 DE2459630 C3 DE 2459630C3
- Authority
- DE
- Germany
- Prior art keywords
- pyrimidyl
- dimethyl
- methoxyergoline
- preparation
- aminomethyl
- Prior art date
- 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
Links
- AGPCNAZOYLBSMB-ZUZSALNQSA-N NCC(C1)CN[C@H](CC2=C(C3=NC=CC=N3)N3)[C@H]1C1=C2C3=CC=C1 Chemical class NCC(C1)CN[C@H](CC2=C(C3=NC=CC=N3)N3)[C@H]1C1=C2C3=CC=C1 AGPCNAZOYLBSMB-ZUZSALNQSA-N 0.000 title claims description 3
- 238000000034 method Methods 0.000 title description 8
- 238000002360 preparation method Methods 0.000 title description 4
- 239000008177 pharmaceutical agent Substances 0.000 title description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 150000001875 compounds Chemical class 0.000 description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 6
- CTEWKXYQIKKNAH-HCGVIMEBSA-N (6ar,10ar)-9-methoxy-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline Chemical compound C1=CC([C@@H]2[C@H](NCC(C2)OC)C2)=C3C2=CNC3=C1 CTEWKXYQIKKNAH-HCGVIMEBSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 230000002908 adrenolytic effect Effects 0.000 description 4
- 230000000202 analgesic effect Effects 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 125000004093 cyano group Chemical group *C#N 0.000 description 3
- 229960004193 dextropropoxyphene Drugs 0.000 description 3
- XLMALTXPSGQGBX-GCJKJVERSA-N dextropropoxyphene Chemical compound C([C@](OC(=O)CC)([C@H](C)CN(C)C)C=1C=CC=CC=1)C1=CC=CC=C1 XLMALTXPSGQGBX-GCJKJVERSA-N 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 229960005181 morphine Drugs 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 235000010446 mineral oil Nutrition 0.000 description 2
- LJXQPZWIHJMPQQ-UHFFFAOYSA-N pyrimidin-2-amine Chemical compound NC1=NC=CC=N1 LJXQPZWIHJMPQQ-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- SEUSFEKWVIFWTN-UHFFFAOYSA-N 2-aminopyrimidine-5-carbonitrile Chemical compound NC1=NC=C(C#N)C=N1 SEUSFEKWVIFWTN-UHFFFAOYSA-N 0.000 description 1
- ZFFBIQMNKOJDJE-UHFFFAOYSA-N 2-bromo-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(Br)C(=O)C1=CC=CC=C1 ZFFBIQMNKOJDJE-UHFFFAOYSA-N 0.000 description 1
- UHRHPPKWXSNZLR-UHFFFAOYSA-N 5-bromopyrimidin-2-amine Chemical compound NC1=NC=C(Br)C=N1 UHRHPPKWXSNZLR-UHFFFAOYSA-N 0.000 description 1
- MHZNCOBCMWBPPM-UHFFFAOYSA-N 5-methylpyrimidin-2-amine Chemical compound CC1=CN=C(N)N=C1 MHZNCOBCMWBPPM-UHFFFAOYSA-N 0.000 description 1
- SSHFCFRJYJIJDV-UHFFFAOYSA-N 5-nitropyrimidin-2-amine Chemical compound NC1=NC=C([N+]([O-])=O)C=N1 SSHFCFRJYJIJDV-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
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000003420 antiserotonin agent Substances 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- HESHRHUZIWVEAJ-JGRZULCMSA-N dihydroergotamine Chemical compound C([C@H]1C(=O)N2CCC[C@H]2[C@]2(O)O[C@@](C(N21)=O)(C)NC(=O)[C@H]1CN([C@H]2[C@@H](C3=CC=CC4=NC=C([C]34)C2)C1)C)C1=CC=CC=C1 HESHRHUZIWVEAJ-JGRZULCMSA-N 0.000 description 1
- 229960004704 dihydroergotamine Drugs 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000006575 electron-withdrawing group Chemical group 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- 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
- A61P25/04—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
- A61P25/20—Hypnotics; Sedatives
-
- 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
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pain & Pain Management (AREA)
- Anesthesiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Coloring (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT5453373 | 1973-12-21 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2459630A1 DE2459630A1 (de) | 1975-07-03 |
| DE2459630B2 DE2459630B2 (de) | 1980-07-10 |
| DE2459630C3 true DE2459630C3 (de) | 1981-05-07 |
Family
ID=11287369
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2459630A Expired DE2459630C3 (de) | 1973-12-21 | 1974-12-17 | 2-Pyrimidyl-aminomethylergolinderivate, Verfahren zu ihrer Herstellung und pharmazeutische Mittel |
Country Status (15)
| Country | Link |
|---|---|
| JP (1) | JPS6027676B2 (enExample) |
| AT (1) | AT345997B (enExample) |
| BE (1) | BE823715A (enExample) |
| CA (1) | CA1033725A (enExample) |
| CH (1) | CH609345A5 (enExample) |
| DE (1) | DE2459630C3 (enExample) |
| DK (1) | DK138895B (enExample) |
| FR (1) | FR2255072B1 (enExample) |
| GB (1) | GB1436820A (enExample) |
| HU (1) | HU168767B (enExample) |
| NL (1) | NL7416120A (enExample) |
| SE (1) | SE417966B (enExample) |
| SU (1) | SU604492A3 (enExample) |
| YU (1) | YU335774A (enExample) |
| ZA (1) | ZA748053B (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1192260B (it) * | 1977-07-05 | 1988-03-31 | Simes | Derivati di ergoline-2-tioeteri e loro solfossidi |
| GB2112382B (en) * | 1981-11-06 | 1985-03-06 | Erba Farmitalia | Ergoline derivatives |
| GB2120242A (en) * | 1982-04-30 | 1983-11-30 | Erba Farmitalia | Ergoline derivatives |
| PH21123A (en) * | 1983-04-28 | 1987-07-27 | Erba Farmitalia | Ergoline derivatives |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5126479Y2 (enExample) * | 1971-11-18 | 1976-07-05 | ||
| BE792188A (fr) * | 1971-12-02 | 1973-06-01 | Farmaceutici Italia | Derives de l'ergoline |
-
1974
- 1974-12-11 NL NL7416120A patent/NL7416120A/xx unknown
- 1974-12-13 GB GB5408174A patent/GB1436820A/en not_active Expired
- 1974-12-16 CA CA216,603A patent/CA1033725A/en not_active Expired
- 1974-12-17 DE DE2459630A patent/DE2459630C3/de not_active Expired
- 1974-12-17 YU YU03357/74A patent/YU335774A/xx unknown
- 1974-12-18 FR FR7441750A patent/FR2255072B1/fr not_active Expired
- 1974-12-18 ZA ZA00748053A patent/ZA748053B/xx unknown
- 1974-12-18 JP JP49144603A patent/JPS6027676B2/ja not_active Expired
- 1974-12-18 AT AT1010974A patent/AT345997B/de not_active IP Right Cessation
- 1974-12-18 HU HUFA971A patent/HU168767B/hu unknown
- 1974-12-19 SE SE7416084A patent/SE417966B/xx not_active IP Right Cessation
- 1974-12-19 DK DK664474AA patent/DK138895B/da not_active IP Right Cessation
- 1974-12-20 SU SU742086147A patent/SU604492A3/ru active
- 1974-12-20 BE BE151819A patent/BE823715A/xx not_active IP Right Cessation
- 1974-12-20 CH CH1714874A patent/CH609345A5/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| YU335774A (en) | 1982-05-31 |
| CH609345A5 (en) | 1979-02-28 |
| BE823715A (fr) | 1975-06-20 |
| DK138895B (da) | 1978-11-13 |
| FR2255072A1 (enExample) | 1975-07-18 |
| SE7416084L (enExample) | 1975-06-23 |
| GB1436820A (en) | 1976-05-26 |
| ATA1010974A (de) | 1978-02-15 |
| AT345997B (de) | 1978-10-10 |
| JPS5095299A (enExample) | 1975-07-29 |
| JPS6027676B2 (ja) | 1985-06-29 |
| NL7416120A (nl) | 1975-06-24 |
| DE2459630B2 (de) | 1980-07-10 |
| AU7659174A (en) | 1976-06-24 |
| CA1033725A (en) | 1978-06-27 |
| SE417966B (sv) | 1981-04-27 |
| HU168767B (enExample) | 1976-07-28 |
| SU604492A3 (ru) | 1978-04-25 |
| DK664474A (enExample) | 1975-09-08 |
| FR2255072B1 (enExample) | 1978-07-28 |
| DK138895C (enExample) | 1979-04-30 |
| DE2459630A1 (de) | 1975-07-03 |
| ZA748053B (en) | 1976-01-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OGA | New person/name/address of the applicant | ||
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |