FI66595C - Foerfarande foer framstaellning av terapeutiskt anvaendbara 2-minocyklopent-1-en-1-tiokarbonyldisulfider - Google Patents
Foerfarande foer framstaellning av terapeutiskt anvaendbara 2-minocyklopent-1-en-1-tiokarbonyldisulfider Download PDFInfo
- Publication number
- FI66595C FI66595C FI773967A FI773967A FI66595C FI 66595 C FI66595 C FI 66595C FI 773967 A FI773967 A FI 773967A FI 773967 A FI773967 A FI 773967A FI 66595 C FI66595 C FI 66595C
- Authority
- FI
- Finland
- Prior art keywords
- dopamine
- acid
- ene
- noradrenaline
- hydroxylase
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 11
- 238000002360 preparation method Methods 0.000 title claims description 6
- 230000001225 therapeutic effect Effects 0.000 title description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 3
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 38
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 33
- SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 24
- 229960002748 norepinephrine Drugs 0.000 description 24
- SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 24
- 229960003638 dopamine Drugs 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- 150000001875 compounds Chemical class 0.000 description 18
- 239000000243 solution Substances 0.000 description 17
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 14
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 12
- UCTWMZQNUQWSLP-UHFFFAOYSA-N adrenaline Chemical compound CNCC(O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- 108010015720 Dopamine beta-Hydroxylase Proteins 0.000 description 11
- 102100033156 Dopamine beta-hydroxylase Human genes 0.000 description 11
- DUUGKQCEGZLZNO-UHFFFAOYSA-N 5-hydroxyindoleacetic acid Chemical compound C1=C(O)C=C2C(CC(=O)O)=CNC2=C1 DUUGKQCEGZLZNO-UHFFFAOYSA-N 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 10
- 210000004556 brain Anatomy 0.000 description 9
- 230000002401 inhibitory effect Effects 0.000 description 9
- 241000699666 Mus <mouse, genus> Species 0.000 description 7
- 229940076279 serotonin Drugs 0.000 description 7
- -1 2-aminocyclopent-1-en-1-thiocarbonyl Chemical group 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- AUZONCFQVSMFAP-UHFFFAOYSA-N disulfiram Chemical compound CCN(CC)C(=S)SSC(=S)N(CC)CC AUZONCFQVSMFAP-UHFFFAOYSA-N 0.000 description 6
- 210000002216 heart Anatomy 0.000 description 6
- 239000003112 inhibitor Substances 0.000 description 6
- 210000000952 spleen Anatomy 0.000 description 6
- DGMPVYSXXIOGJY-UHFFFAOYSA-N Fusaric acid Chemical compound CCCCC1=CC=C(C(O)=O)N=C1 DGMPVYSXXIOGJY-UHFFFAOYSA-N 0.000 description 5
- 241000699670 Mus sp. Species 0.000 description 5
- 238000003556 assay Methods 0.000 description 5
- 239000012153 distilled water Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 210000004100 adrenal gland Anatomy 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 150000003943 catecholamines Chemical class 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 210000005036 nerve Anatomy 0.000 description 4
- 210000000056 organ Anatomy 0.000 description 4
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 4
- SPZDBFZHUCNYLS-UHFFFAOYSA-N (2-aminocyclopentene-1-carbothioyl)sulfanyl 2-aminocyclopentene-1-carbodithioate Chemical class C1CCC(N)=C1C(=S)SSC(=S)C1=C(N)CCC1 SPZDBFZHUCNYLS-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- KSRBLMBTFSXSBM-UHFFFAOYSA-N [2-(ethylamino)cyclopentene-1-carbothioyl]sulfanyl 2-(ethylamino)cyclopentene-1-carbodithioate Chemical compound C1CCC(NCC)=C1C(=S)SSC(=S)C1=C(NCC)CCC1 KSRBLMBTFSXSBM-UHFFFAOYSA-N 0.000 description 3
- LMBWSYZSUOEYSN-UHFFFAOYSA-N diethyldithiocarbamic acid Chemical compound CCN(CC)C(S)=S LMBWSYZSUOEYSN-UHFFFAOYSA-N 0.000 description 3
- 229960002563 disulfiram Drugs 0.000 description 3
- 230000005284 excitation Effects 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 238000007912 intraperitoneal administration Methods 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 239000006228 supernatant Substances 0.000 description 3
- 238000011282 treatment Methods 0.000 description 3
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 3
- NXJOFTRBTBDSHB-UHFFFAOYSA-N (4-methyl-1,4-diazepane-1-carbothioyl)sulfanyl 4-methyl-1,4-diazepane-1-carbodithioate Chemical compound C1CN(C)CCCN1C(=S)SSC(=S)N1CCN(C)CCC1 NXJOFTRBTBDSHB-UHFFFAOYSA-N 0.000 description 2
- GCZZOZBWAZHCAN-UHFFFAOYSA-N 1-phenyl-3-(1,3-thiazol-2-yl)thiourea Chemical compound C=1C=CC=CC=1NC(=S)NC1=NC=CS1 GCZZOZBWAZHCAN-UHFFFAOYSA-N 0.000 description 2
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- 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
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 2
- RPTUSVTUFVMDQK-UHFFFAOYSA-N Hidralazin Chemical compound C1=CC=C2C(NN)=NN=CC2=C1 RPTUSVTUFVMDQK-UHFFFAOYSA-N 0.000 description 2
- 108010093488 His-His-His-His-His-His Proteins 0.000 description 2
- 241000906446 Theraps Species 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- OEWKQEHUGWGZKS-UHFFFAOYSA-N [2-(cyclohexylamino)cyclopentene-1-carbothioyl]sulfanyl 2-(cyclohexylamino)cyclopentene-1-carbodithioate Chemical compound C1(CCCCC1)NC1=C(CCC1)C(=S)SSC(=S)C1=C(CCC1)NC1CCCCC1 OEWKQEHUGWGZKS-UHFFFAOYSA-N 0.000 description 2
- 239000008186 active pharmaceutical agent Substances 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000000908 ammonium hydroxide Substances 0.000 description 2
- 229950004394 ditiocarb Drugs 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 230000002474 noradrenergic effect Effects 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- ZWLUXSQADUDCSB-UHFFFAOYSA-N phthalaldehyde Chemical compound O=CC1=CC=CC=C1C=O ZWLUXSQADUDCSB-UHFFFAOYSA-N 0.000 description 2
- 230000003389 potentiating effect Effects 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 235000010265 sodium sulphite Nutrition 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- SPFUGDSFNDDSBJ-UHFFFAOYSA-N (2-aminocyclopenten-1-yl)-[bis(sulfanylidene)-$l^{6}-sulfanylidene]methanol Chemical class NC1=C(C(O)=S(=S)=S)CCC1 SPFUGDSFNDDSBJ-UHFFFAOYSA-N 0.000 description 1
- XMPRFBUTGLVJQS-HTQCVBHVSA-N (E)-[(2S)-1-[[(E)-but-2-enoyl]amino]-3-methylbutan-2-yl]-hydroxyimino-oxidoazanium Chemical compound C\C=C\C(=O)NC[C@H](C(C)C)[N+](\[O-])=N/O XMPRFBUTGLVJQS-HTQCVBHVSA-N 0.000 description 1
- KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 description 1
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- WFIYPADYPQQLNN-UHFFFAOYSA-N 2-[2-(4-bromopyrazol-1-yl)ethyl]isoindole-1,3-dione Chemical compound C1=C(Br)C=NN1CCN1C(=O)C2=CC=CC=C2C1=O WFIYPADYPQQLNN-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- QYPKEVDTCBHOMB-UHFFFAOYSA-N ClC=1N=C(C(=O)O)C=CC1CCC Chemical compound ClC=1N=C(C(=O)O)C=CC1CCC QYPKEVDTCBHOMB-UHFFFAOYSA-N 0.000 description 1
- FJUBKTNNXRFHFD-WTSVBCDHSA-N Dopastin Natural products C\C=C\C(=O)NC[C@H](C(C)C)N(O)N=O FJUBKTNNXRFHFD-WTSVBCDHSA-N 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 108010074633 Mixed Function Oxygenases Proteins 0.000 description 1
- 102000008109 Mixed Function Oxygenases Human genes 0.000 description 1
- OFELWPIUPPMBTA-UHFFFAOYSA-N Oosponol Natural products OCC(=O)C1=Cc2cccc(O)c2C(=O)O1 OFELWPIUPPMBTA-UHFFFAOYSA-N 0.000 description 1
- 208000018737 Parkinson disease Diseases 0.000 description 1
- RUZDWVDIAHNLGQ-UHFFFAOYSA-N [2-(butylamino)cyclopentene-1-carbothioyl]sulfanyl 2-(butylamino)cyclopentene-1-carbodithioate Chemical compound C(CCC)NC1=C(CCC1)C(=S)SSC(=S)C1=C(CCC1)NCCCC RUZDWVDIAHNLGQ-UHFFFAOYSA-N 0.000 description 1
- 210000000683 abdominal cavity Anatomy 0.000 description 1
- 230000003187 abdominal effect Effects 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 229940025084 amphetamine Drugs 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- NHOWLEZFTHYCTP-UHFFFAOYSA-N benzylhydrazine Chemical compound NNCC1=CC=CC=C1 NHOWLEZFTHYCTP-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 229940116901 diethyldithiocarbamate Drugs 0.000 description 1
- 150000002019 disulfides Chemical class 0.000 description 1
- 239000012990 dithiocarbamate Substances 0.000 description 1
- 150000004659 dithiocarbamates Chemical class 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229960002474 hydralazine Drugs 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 238000011866 long-term treatment Methods 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- PMRYVIKBURPHAH-UHFFFAOYSA-N methimazole Chemical compound CN1C=CNC1=S PMRYVIKBURPHAH-UHFFFAOYSA-N 0.000 description 1
- 210000000653 nervous system Anatomy 0.000 description 1
- XYEOALKITRFCJJ-UHFFFAOYSA-N o-benzylhydroxylamine Chemical compound NOCC1=CC=CC=C1 XYEOALKITRFCJJ-UHFFFAOYSA-N 0.000 description 1
- WRIZJEREXIDJCC-UHFFFAOYSA-N oosponol Chemical compound C1=CC=C2C(C(=O)CO)=COC(=O)C2=C1O WRIZJEREXIDJCC-UHFFFAOYSA-N 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 239000013558 reference substance Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000003393 splenic effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 210000002820 sympathetic nervous system Anatomy 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 229960002178 thiamazole Drugs 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
-
- 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
- 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)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Epidemiology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU76RI610A HU175526B (hu) | 1976-12-30 | 1976-12-30 | Sposob poluchenija 2-amino-ciklopent-1-en-1-ditiokarbonovykh-disul'fidov |
| HURI000610 | 1976-12-30 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI773967A7 FI773967A7 (fi) | 1978-07-01 |
| FI66595B FI66595B (fi) | 1984-07-31 |
| FI66595C true FI66595C (fi) | 1984-11-12 |
Family
ID=11001014
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI773967A FI66595C (fi) | 1976-12-30 | 1977-12-29 | Foerfarande foer framstaellning av terapeutiskt anvaendbara 2-minocyklopent-1-en-1-tiokarbonyldisulfider |
Country Status (21)
| Country | Link |
|---|---|
| JP (1) | JPS5384949A (enExample) |
| AR (1) | AR216308A1 (enExample) |
| AT (1) | AT351501B (enExample) |
| AU (1) | AU516353B2 (enExample) |
| BE (1) | BE862408A (enExample) |
| CH (1) | CH631701A5 (enExample) |
| DE (1) | DE2758809A1 (enExample) |
| ES (1) | ES465567A1 (enExample) |
| FI (1) | FI66595C (enExample) |
| FR (1) | FR2376132A1 (enExample) |
| GB (1) | GB1582716A (enExample) |
| HU (1) | HU175526B (enExample) |
| IL (1) | IL53646A (enExample) |
| IN (1) | IN146470B (enExample) |
| NL (1) | NL7714514A (enExample) |
| NO (1) | NO145237C (enExample) |
| PT (1) | PT67482B (enExample) |
| SE (1) | SE7714526L (enExample) |
| SU (1) | SU743580A3 (enExample) |
| YU (1) | YU309677A (enExample) |
| ZA (1) | ZA777573B (enExample) |
-
1976
- 1976-12-30 HU HU76RI610A patent/HU175526B/hu unknown
-
1977
- 1977-12-19 IL IL53646A patent/IL53646A/xx unknown
- 1977-12-20 AT AT912077A patent/AT351501B/de not_active IP Right Cessation
- 1977-12-20 SE SE7714526A patent/SE7714526L/ not_active Application Discontinuation
- 1977-12-20 ZA ZA00777573A patent/ZA777573B/xx unknown
- 1977-12-21 CH CH1582477A patent/CH631701A5/de not_active IP Right Cessation
- 1977-12-23 AU AU31979/77A patent/AU516353B2/en not_active Expired
- 1977-12-26 FR FR7739183A patent/FR2376132A1/fr active Granted
- 1977-12-27 IN IN1772/CAL/77A patent/IN146470B/en unknown
- 1977-12-27 YU YU03096/77A patent/YU309677A/xx unknown
- 1977-12-28 BE BE183912A patent/BE862408A/xx not_active IP Right Cessation
- 1977-12-28 SU SU772559902A patent/SU743580A3/ru active
- 1977-12-29 ES ES465567A patent/ES465567A1/es not_active Expired
- 1977-12-29 GB GB54173/77A patent/GB1582716A/en not_active Expired
- 1977-12-29 PT PT67482A patent/PT67482B/pt unknown
- 1977-12-29 JP JP15853077A patent/JPS5384949A/ja active Pending
- 1977-12-29 AR AR270573A patent/AR216308A1/es active
- 1977-12-29 FI FI773967A patent/FI66595C/fi not_active IP Right Cessation
- 1977-12-29 NO NO774502A patent/NO145237C/no unknown
- 1977-12-29 NL NL7714514A patent/NL7714514A/xx not_active Application Discontinuation
- 1977-12-30 DE DE19772758809 patent/DE2758809A1/de not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| FI66595B (fi) | 1984-07-31 |
| SU743580A3 (ru) | 1980-06-25 |
| IL53646A0 (en) | 1978-03-10 |
| ATA912077A (de) | 1979-01-15 |
| AU516353B2 (en) | 1981-05-28 |
| NL7714514A (nl) | 1978-07-04 |
| AR216308A1 (es) | 1979-12-14 |
| CH631701A5 (en) | 1982-08-31 |
| NO145237C (no) | 1982-02-10 |
| PT67482A (en) | 1978-01-01 |
| YU309677A (en) | 1983-01-21 |
| FI773967A7 (fi) | 1978-07-01 |
| HU175526B (hu) | 1980-08-28 |
| AU3197977A (en) | 1979-06-28 |
| PT67482B (en) | 1979-05-30 |
| AT351501B (de) | 1979-07-25 |
| BE862408A (fr) | 1978-04-14 |
| GB1582716A (en) | 1981-01-14 |
| FR2376132B1 (enExample) | 1979-10-19 |
| IL53646A (en) | 1982-03-31 |
| NO774502L (no) | 1978-07-03 |
| NO145237B (no) | 1981-11-02 |
| IN146470B (enExample) | 1979-06-09 |
| ES465567A1 (es) | 1979-01-01 |
| FR2376132A1 (fr) | 1978-07-28 |
| DE2758809A1 (de) | 1978-07-06 |
| ZA777573B (en) | 1978-10-25 |
| JPS5384949A (en) | 1978-07-26 |
| SE7714526L (sv) | 1978-07-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: RICHTER GEDEON VEGYESZETI GYAR R. T. |