CS219272B2 - Method of making the 5/10-9/-abeo-ergoline derivatives - Google Patents
Method of making the 5/10-9/-abeo-ergoline derivatives Download PDFInfo
- Publication number
- CS219272B2 CS219272B2 CS801783A CS178380A CS219272B2 CS 219272 B2 CS219272 B2 CS 219272B2 CS 801783 A CS801783 A CS 801783A CS 178380 A CS178380 A CS 178380A CS 219272 B2 CS219272 B2 CS 219272B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- group
- formula
- compound
- compounds
- abeo
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 83
- -1 piperidinocarbonyl Chemical group 0.000 claims abstract description 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 13
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 7
- 125000006518 morpholino carbonyl group Chemical group [H]C1([H])OC([H])([H])C([H])([H])N(C(*)=O)C1([H])[H] 0.000 claims abstract description 7
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims abstract description 6
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- 125000005117 dialkylcarbamoyl group Chemical group 0.000 claims abstract description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 6
- 239000001257 hydrogen Substances 0.000 claims abstract description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 5
- 150000003839 salts Chemical class 0.000 claims abstract description 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 3
- 229910052731 fluorine Chemical group 0.000 claims abstract description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 3
- 238000002360 preparation method Methods 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 25
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 18
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 13
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 9
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 8
- 229910021529 ammonia Inorganic materials 0.000 claims description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N dimethyl sulfoxide Natural products CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 5
- 150000003973 alkyl amines Chemical class 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 239000003880 polar aprotic solvent Substances 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 125000005265 dialkylamine group Chemical group 0.000 claims description 3
- 230000032050 esterification Effects 0.000 claims description 2
- 238000005886 esterification reaction Methods 0.000 claims description 2
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical group [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 claims 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims 1
- 238000009833 condensation Methods 0.000 claims 1
- 230000005494 condensation Effects 0.000 claims 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 claims 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 5
- 230000003276 anti-hypertensive effect Effects 0.000 abstract description 3
- 231100000053 low toxicity Toxicity 0.000 abstract description 2
- 230000001225 therapeutic effect Effects 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- RPTUSVTUFVMDQK-UHFFFAOYSA-N Hidralazin Chemical compound C1=CC=C2C(NN)=NN=CC2=C1 RPTUSVTUFVMDQK-UHFFFAOYSA-N 0.000 description 22
- 239000006260 foam Substances 0.000 description 14
- 230000036772 blood pressure Effects 0.000 description 12
- 230000000694 effects Effects 0.000 description 12
- 229960002474 hydralazine Drugs 0.000 description 11
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 241000700159 Rattus Species 0.000 description 8
- 239000000243 solution Substances 0.000 description 7
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
- 206010020772 Hypertension Diseases 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- 230000001631 hypertensive effect Effects 0.000 description 4
- 229940080818 propionamide Drugs 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- CJCSPKMFHVPWAR-JTQLQIEISA-N alpha-methyl-L-dopa Chemical compound OC(=O)[C@](N)(C)CC1=CC=C(O)C(O)=C1 CJCSPKMFHVPWAR-JTQLQIEISA-N 0.000 description 3
- 210000001715 carotid artery Anatomy 0.000 description 3
- 238000006114 decarboxylation reaction Methods 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 3
- 125000004494 ethyl ester group Chemical group 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000011699 spontaneously hypertensive rat Methods 0.000 description 3
- 231100000419 toxicity Toxicity 0.000 description 3
- 230000001988 toxicity Effects 0.000 description 3
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
- HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical compound OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 230000036471 bradycardia Effects 0.000 description 2
- 208000006218 bradycardia Diseases 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 231100000673 dose–response relationship Toxicity 0.000 description 2
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 238000001640 fractional crystallisation Methods 0.000 description 2
- 238000003304 gavage Methods 0.000 description 2
- 229960002897 heparin Drugs 0.000 description 2
- 229920000669 heparin Polymers 0.000 description 2
- 230000001077 hypotensive effect Effects 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 239000002504 physiological saline solution Substances 0.000 description 2
- 230000003389 potentiating effect Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- YEJJUJNTWYKFLS-UHFFFAOYSA-N 1-pyrrolidin-1-ylpropan-1-one Chemical compound CCC(=O)N1CCCC1 YEJJUJNTWYKFLS-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 206010002091 Anaesthesia Diseases 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- QCOGKXLOEWLIDC-UHFFFAOYSA-N N-methylbutylamine Chemical compound CCCCNC QCOGKXLOEWLIDC-UHFFFAOYSA-N 0.000 description 1
- 206010058667 Oral toxicity Diseases 0.000 description 1
- QGMRQYFBGABWDR-UHFFFAOYSA-M Pentobarbital sodium Chemical compound [Na+].CCCC(C)C1(CC)C(=O)NC(=O)[N-]C1=O QGMRQYFBGABWDR-UHFFFAOYSA-M 0.000 description 1
- 241000978776 Senegalia senegal Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 208000001871 Tachycardia Diseases 0.000 description 1
- 102100033121 Transcription factor 21 Human genes 0.000 description 1
- 101710119687 Transcription factor 21 Proteins 0.000 description 1
- ZVQOOHYFBIDMTQ-UHFFFAOYSA-N [methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide Chemical compound N#CN=S(C)(=O)C(C)C1=CC=C(C(F)(F)F)N=C1 ZVQOOHYFBIDMTQ-UHFFFAOYSA-N 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 229940030600 antihypertensive agent Drugs 0.000 description 1
- 239000002220 antihypertensive agent Substances 0.000 description 1
- 210000001367 artery Anatomy 0.000 description 1
- 238000009530 blood pressure measurement Methods 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- 229940083181 centrally acting adntiadrenergic agent methyldopa Drugs 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001647 drug administration Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 230000000095 emetic effect Effects 0.000 description 1
- ZIUSEGSNTOUIPT-UHFFFAOYSA-N ethyl 2-cyanoacetate Chemical compound CCOC(=O)CC#N ZIUSEGSNTOUIPT-UHFFFAOYSA-N 0.000 description 1
- CXDGRSYTPLHQMC-UHFFFAOYSA-N ethyl 2-cyanoacetate;sodium Chemical compound [Na].CCOC(=O)CC#N CXDGRSYTPLHQMC-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 229960004502 levodopa Drugs 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- ZFNAETKJDHAQEN-UHFFFAOYSA-N n-benzylpropanamide Chemical compound CCC(=O)NCC1=CC=CC=C1 ZFNAETKJDHAQEN-UHFFFAOYSA-N 0.000 description 1
- ABMDIECEEGFXNC-UHFFFAOYSA-N n-ethylpropanamide Chemical compound CCNC(=O)CC ABMDIECEEGFXNC-UHFFFAOYSA-N 0.000 description 1
- 231100000418 oral toxicity Toxicity 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 229960002275 pentobarbital sodium Drugs 0.000 description 1
- 230000002980 postoperative effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 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
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000006794 tachycardia Effects 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- 230000002618 waking effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/06—Peri-condensed systems
-
- 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
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Medicinal Chemistry (AREA)
- Cardiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Heart & Thoracic Surgery (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Steroid Compounds (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB7909281 | 1979-03-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS219272B2 true CS219272B2 (en) | 1983-03-25 |
Family
ID=10503915
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS801783A CS219272B2 (en) | 1979-03-16 | 1980-03-14 | Method of making the 5/10-9/-abeo-ergoline derivatives |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US4317912A (ru) |
| EP (1) | EP0016411B1 (ru) |
| JP (1) | JPS55124784A (ru) |
| AT (1) | ATE1598T1 (ru) |
| AU (1) | AU526978B2 (ru) |
| CA (1) | CA1132555A (ru) |
| CS (1) | CS219272B2 (ru) |
| DE (1) | DE3060888D1 (ru) |
| DK (1) | DK154887C (ru) |
| FI (1) | FI66871C (ru) |
| HU (1) | HU179840B (ru) |
| IE (1) | IE49556B1 (ru) |
| IL (1) | IL59507A (ru) |
| IT (1) | IT1196406B (ru) |
| SU (1) | SU971100A3 (ru) |
| YU (1) | YU70180A (ru) |
| ZA (1) | ZA801505B (ru) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8419278D0 (en) * | 1984-07-27 | 1984-08-30 | Lilly Industries Ltd | Pharmaceutical compounds |
| US4835313A (en) * | 1986-03-03 | 1989-05-30 | Merck & Co., Inc. | (5,6-dichloro-3-oxo-9α-propyl-2,3,9,9α-tetrahydrofluoren-7-yl) alkanimidamides |
| US4731472A (en) * | 1986-03-03 | 1988-03-15 | Merck & Co., Inc. | (5,6-dichloro-3-oxo-9A-propyl-2,3,9,9A-tetrahydrofluoren-7-yl)alkanoic acids and alkanimidamides |
| GB8608893D0 (en) * | 1986-04-11 | 1986-05-14 | Erba Farmitalia | D-nor-7-ergoline derivatives |
| GB8617907D0 (en) * | 1986-07-22 | 1986-08-28 | Erba Farmitalia | Tetracyclic indole derivatives |
| US5054490A (en) * | 1988-05-11 | 1991-10-08 | Lunar Corporation | Ultrasonic densitometer device and method |
| GB9407637D0 (en) | 1994-04-18 | 1994-06-08 | Erba Carlo Spa | Serotoninergic abeo-ergoline derivatives |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1482871A (en) * | 1922-12-01 | 1924-02-05 | Smith Lulu Teeter | Child's music rack |
| US3393208A (en) * | 1965-10-22 | 1968-07-16 | Mcneilab Inc | 6h-benzo[5, 6] cyclohept[1, 2, 3-cd]indolin-1, 6-diones |
| US3397202A (en) * | 1967-05-02 | 1968-08-13 | Mcneilab Inc | 11, 11alpha-dihydro-11alpha-hydroxy-2-(lower alkyl)-11-r3-6eta-benzo [5, 6] cyclohept [1, 2, 3-cd] indolin-1, 6-diones and intermediates for their preparation |
| GB1482871A (en) * | 1975-03-18 | 1977-08-17 | Farmaceutici Italia | Tetracyclic indole derivatives |
-
1980
- 1980-02-29 IL IL59507A patent/IL59507A/xx unknown
- 1980-03-11 US US06/129,333 patent/US4317912A/en not_active Expired - Lifetime
- 1980-03-11 AU AU56311/80A patent/AU526978B2/en not_active Ceased
- 1980-03-12 AT AT80101273T patent/ATE1598T1/de not_active IP Right Cessation
- 1980-03-12 EP EP80101273A patent/EP0016411B1/en not_active Expired
- 1980-03-12 JP JP3044780A patent/JPS55124784A/ja active Pending
- 1980-03-12 DE DE8080101273T patent/DE3060888D1/de not_active Expired
- 1980-03-13 DK DK108580A patent/DK154887C/da active
- 1980-03-13 CA CA347,558A patent/CA1132555A/en not_active Expired
- 1980-03-14 SU SU802892378A patent/SU971100A3/ru active
- 1980-03-14 ZA ZA00801505A patent/ZA801505B/xx unknown
- 1980-03-14 IE IE541/80A patent/IE49556B1/en unknown
- 1980-03-14 YU YU00701/80A patent/YU70180A/xx unknown
- 1980-03-14 HU HU8080611A patent/HU179840B/hu not_active IP Right Cessation
- 1980-03-14 IT IT20667/80A patent/IT1196406B/it active
- 1980-03-14 CS CS801783A patent/CS219272B2/cs unknown
- 1980-03-14 FI FI800792A patent/FI66871C/fi not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| IT8020667A0 (it) | 1980-03-14 |
| ZA801505B (en) | 1981-05-27 |
| FI800792A (fi) | 1980-09-17 |
| DK154887B (da) | 1989-01-02 |
| DE3060888D1 (en) | 1982-11-11 |
| IL59507A0 (en) | 1980-05-30 |
| IE49556B1 (en) | 1985-10-30 |
| IE800541L (en) | 1980-09-16 |
| FI66871C (fi) | 1984-12-10 |
| HU179840B (en) | 1982-12-28 |
| ATE1598T1 (de) | 1982-10-15 |
| FI66871B (fi) | 1984-08-31 |
| AU526978B2 (en) | 1983-02-10 |
| US4317912A (en) | 1982-03-02 |
| YU70180A (en) | 1983-02-28 |
| SU971100A3 (ru) | 1982-10-30 |
| IL59507A (en) | 1984-01-31 |
| EP0016411A3 (en) | 1980-11-26 |
| AU5631180A (en) | 1980-09-18 |
| CA1132555A (en) | 1982-09-28 |
| DK154887C (da) | 1989-07-03 |
| IT1196406B (it) | 1988-11-16 |
| JPS55124784A (en) | 1980-09-26 |
| EP0016411A2 (en) | 1980-10-01 |
| DK108580A (da) | 1980-09-17 |
| EP0016411B1 (en) | 1982-09-29 |
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