GB2060639A - Novel oxayohimbane derivatives useful in therapy - Google Patents
Novel oxayohimbane derivatives useful in therapy Download PDFInfo
- Publication number
- GB2060639A GB2060639A GB8032835A GB8032835A GB2060639A GB 2060639 A GB2060639 A GB 2060639A GB 8032835 A GB8032835 A GB 8032835A GB 8032835 A GB8032835 A GB 8032835A GB 2060639 A GB2060639 A GB 2060639A
- Authority
- GB
- United Kingdom
- Prior art keywords
- formula
- radical
- compound
- oxayohimbane
- hydrogen
- 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.)
- Withdrawn
Links
- 238000002560 therapeutic procedure Methods 0.000 title abstract description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 34
- 239000001257 hydrogen Substances 0.000 claims abstract description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 13
- 239000002253 acid Substances 0.000 claims abstract description 12
- GRTOGORTSDXSFK-XJTZBENFSA-N ajmalicine Chemical compound C1=CC=C2C(CCN3C[C@@H]4[C@H](C)OC=C([C@H]4C[C@H]33)C(=O)OC)=C3NC2=C1 GRTOGORTSDXSFK-XJTZBENFSA-N 0.000 claims abstract description 11
- ZLQMRLSBXKQKMG-UHFFFAOYSA-N rauniticine Natural products COC(=O)C1=CC2CC3N(CCc4c3[nH]c5ccccc45)CC2C(C)O1 ZLQMRLSBXKQKMG-UHFFFAOYSA-N 0.000 claims abstract description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 9
- 150000003839 salts Chemical class 0.000 claims abstract description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 7
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 6
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 6
- 238000000034 method Methods 0.000 claims abstract description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 6
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 5
- 125000005112 cycloalkylalkoxy group Chemical group 0.000 claims abstract description 5
- 125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 5
- 125000005843 halogen group Chemical group 0.000 claims abstract description 5
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 4
- 125000000000 cycloalkoxy group Chemical group 0.000 claims abstract description 4
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims abstract description 3
- 150000001340 alkali metals Chemical class 0.000 claims abstract description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims abstract description 3
- 150000001342 alkaline earth metals Chemical class 0.000 claims abstract description 3
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims abstract description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 3
- BLNWTAHYTCHDJH-UHFFFAOYSA-O hydroxy(oxo)azanium Chemical compound O[NH+]=O BLNWTAHYTCHDJH-UHFFFAOYSA-O 0.000 claims abstract description 3
- 239000002585 base Substances 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 238000005886 esterification reaction Methods 0.000 claims description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 4
- 230000032050 esterification Effects 0.000 claims description 4
- 238000005809 transesterification reaction Methods 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 3
- -1 ethoxy, propoxy Chemical group 0.000 claims description 3
- 150000004820 halides Chemical class 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 150000003973 alkyl amines Chemical class 0.000 claims description 2
- 229910021529 ammonia Inorganic materials 0.000 claims description 2
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 2
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 2
- 125000005265 dialkylamine group Chemical group 0.000 claims description 2
- 239000012458 free base Substances 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 206010000117 Abnormal behaviour Diseases 0.000 abstract description 2
- 208000012886 Vertigo Diseases 0.000 abstract description 2
- 230000001037 epileptic effect Effects 0.000 abstract description 2
- 231100000889 vertigo Toxicity 0.000 abstract description 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 6
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 206010002660 Anoxia Diseases 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 206010021143 Hypoxia Diseases 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 230000004083 survival effect Effects 0.000 description 3
- CZJDUZOWQVAEEV-XIEZEKGWSA-N (+)-19-epi-Ajmalicine Natural products O=C(OC)C=1[C@@H]2[C@@H]([C@@H](C)OC=1)C[N+]1[C@H](c3[nH]c4c(c3CC1)cccc4)C2 CZJDUZOWQVAEEV-XIEZEKGWSA-N 0.000 description 2
- 241000976983 Anoxia Species 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 229940007897 ajmalicine Drugs 0.000 description 2
- 230000007953 anoxia Effects 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 208000020401 Depressive disease Diseases 0.000 description 1
- WYTGDNHDOZPMIW-RCBQFDQVSA-N alstonine Natural products C1=CC2=C3C=CC=CC3=NC2=C2N1C[C@H]1[C@H](C)OC=C(C(=O)OC)[C@H]1C2 WYTGDNHDOZPMIW-RCBQFDQVSA-N 0.000 description 1
- 230000009435 amidation Effects 0.000 description 1
- 238000007112 amidation reaction Methods 0.000 description 1
- 238000010640 amide synthesis reaction Methods 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Chemical group 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 230000003970 cerebral vascular damage Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 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
- 238000007796 conventional method Methods 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- VEUUMBGHMNQHGO-UHFFFAOYSA-N ethyl chloroacetate Chemical compound CCOC(=O)CCl VEUUMBGHMNQHGO-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000006213 oxygenation reaction Methods 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 208000009999 tuberous sclerosis Diseases 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/22—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains four or more hetero rings
-
- 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
- A61P25/24—Antidepressants
-
- 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
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
-
- 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
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Psychiatry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Pain & Pain Management (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyesters Or Polycarbonates (AREA)
- Preventing Corrosion Or Incrustation Of Metals (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7925353A FR2467206A1 (fr) | 1979-10-11 | 1979-10-11 | Derives de l'acide oxayohimbane-carboxylique, leur preparation et leur application en therapeutique |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB2060639A true GB2060639A (en) | 1981-05-07 |
Family
ID=9230588
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB8032835A Withdrawn GB2060639A (en) | 1979-10-11 | 1980-10-10 | Novel oxayohimbane derivatives useful in therapy |
Country Status (17)
| Country | Link |
|---|---|
| JP (1) | JPS5661382A (enExample) |
| AU (1) | AU6316580A (enExample) |
| BE (1) | BE885656A (enExample) |
| DE (1) | DE3038401A1 (enExample) |
| DK (1) | DK428780A (enExample) |
| ES (1) | ES8206521A1 (enExample) |
| FR (1) | FR2467206A1 (enExample) |
| GB (1) | GB2060639A (enExample) |
| GR (1) | GR70751B (enExample) |
| IL (1) | IL61246A0 (enExample) |
| IT (1) | IT1195761B (enExample) |
| LU (1) | LU82833A1 (enExample) |
| NL (1) | NL8005609A (enExample) |
| NO (1) | NO803038L (enExample) |
| PT (1) | PT71901B (enExample) |
| SE (1) | SE8007121L (enExample) |
| ZA (1) | ZA806246B (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4125137C2 (de) * | 1991-07-30 | 1995-06-14 | Icos Ges Fuer Ind Communicatio | Steuerpult für Bearbeitungs- und Meßmaschinen |
-
1979
- 1979-10-11 FR FR7925353A patent/FR2467206A1/fr active Granted
-
1980
- 1980-10-09 ZA ZA00806246A patent/ZA806246B/xx unknown
- 1980-10-09 IT IT25251/80A patent/IT1195761B/it active
- 1980-10-09 JP JP14184380A patent/JPS5661382A/ja active Pending
- 1980-10-10 NO NO803038A patent/NO803038L/no unknown
- 1980-10-10 GB GB8032835A patent/GB2060639A/en not_active Withdrawn
- 1980-10-10 BE BE0/202429A patent/BE885656A/fr unknown
- 1980-10-10 DK DK428780A patent/DK428780A/da unknown
- 1980-10-10 ES ES495797A patent/ES8206521A1/es not_active Expired
- 1980-10-10 NL NL8005609A patent/NL8005609A/nl not_active Application Discontinuation
- 1980-10-10 AU AU63165/80A patent/AU6316580A/en not_active Abandoned
- 1980-10-10 PT PT71901A patent/PT71901B/pt unknown
- 1980-10-10 IL IL61246A patent/IL61246A0/xx unknown
- 1980-10-10 LU LU82833A patent/LU82833A1/fr unknown
- 1980-10-10 GR GR63108A patent/GR70751B/el unknown
- 1980-10-10 DE DE19803038401 patent/DE3038401A1/de not_active Withdrawn
- 1980-10-10 SE SE8007121A patent/SE8007121L/xx not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| IL61246A0 (en) | 1980-12-31 |
| FR2467206B1 (enExample) | 1983-01-28 |
| SE8007121L (sv) | 1981-04-12 |
| NO803038L (no) | 1981-04-13 |
| IT1195761B (it) | 1988-10-27 |
| ES495797A0 (es) | 1982-01-16 |
| ES8206521A1 (es) | 1982-01-16 |
| LU82833A1 (fr) | 1982-05-10 |
| JPS5661382A (en) | 1981-05-26 |
| ZA806246B (en) | 1981-10-28 |
| DE3038401A1 (de) | 1981-04-23 |
| IT8025251A0 (it) | 1980-10-09 |
| BE885656A (fr) | 1981-04-10 |
| GR70751B (enExample) | 1983-03-14 |
| PT71901B (fr) | 1981-08-31 |
| NL8005609A (nl) | 1981-04-14 |
| DK428780A (da) | 1981-04-12 |
| PT71901A (fr) | 1980-11-01 |
| AU6316580A (en) | 1981-04-16 |
| FR2467206A1 (fr) | 1981-04-17 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0054951B1 (en) | Dibenz(b,f)(1,4)oxazepine derivatives, process for preparing the same, and pharmaceutical compositions comprising the same | |
| US4730048A (en) | Gut-selective opiates | |
| EP0328000B1 (de) | Indolocarbazol-Derivate, Verfahren zu deren Herstellung und diese enthaltende Arzneimittel | |
| EP0227355B1 (en) | Prodrugs of rapamycin | |
| US6200988B1 (en) | Heterocyclic derivatives and pharmaceutical use thereof | |
| US4806556A (en) | Gut-selective opiates | |
| US4423044A (en) | 3,4-Dihydro-5H-2,3-benzodiazepine derivatives and pharmaceutical use thereof | |
| PL158285B1 (en) | Method of obtaining novel derivatives of 9-(2-hydroxyetoxymethyl-guanine | |
| GB2048268A (en) | Amides of acyl-carnitines process for preparing same and pharmaceutical compositions containing such amides | |
| EP0041355A1 (en) | Novel erythromycin compounds | |
| HU188000B (en) | Process for production of n-2 substituated 9-/1,3 dihydroxi-2-propoxi-methil/-guanins | |
| US4426391A (en) | [(Alkoxycarbonyl)oxy]alkyl esters of methyldopa | |
| GB2158440A (en) | 4,5,6,7-Tetrahydroimidazo[4,5-c]pyridine derivatives | |
| FI92707B (fi) | Menetelmä uusien terapeuttisesti käyttökelpoisten estramustiiniestereiden valmistamiseksi | |
| KR100351952B1 (ko) | 캠프토테신,그제조방법및항종양제 | |
| GB2071091A (en) | Acyl-derivatives of carnitine and the therapeutic use thereof | |
| IL95949A (en) | Process for the preparation of L-) - 3 pyroglutamil (- L-thiolidine-4-carboxylic acid and its history | |
| GB2060639A (en) | Novel oxayohimbane derivatives useful in therapy | |
| EP0669911B1 (en) | Indole derivative having prolonged immunostimulating activity and pharmaceutical compositions therefrom | |
| US5696154A (en) | Brefeldin A derivatives and their utility in the treatment of cancer | |
| GB1603127A (en) | Rifamycin compounds | |
| US5331010A (en) | 1-phenylalkanecarboxylic acid derivatives as anticonvulsant and neuroprotective agents | |
| US4587052A (en) | 1H-pyrrolo-[2,1-C][1,4]benzodiazepine-2-acrylamide compounds having antitumor activity | |
| AU613649B2 (en) | Compositions and methods for promoting growth of animals | |
| WO1993012090A1 (en) | 4-amino-3-acyl quinoline derivatives and their use as inhibitors of gastric acid secretion |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| WAP | Application withdrawn, taken to be withdrawn or refused ** after publication under section 16(1) |